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NEW CRYSTALLINE FORM OF (3R,4R)-(1-BENZYL-4-METHYL-PIPERIDIN-3-YL)-METHYL-(7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)-AMINE

IP.com Disclosure Number: IPCOM000239321D
Publication Date: 2014-Oct-29
Document File: 2 page(s) / 31K

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NEW CRYSTALLINE FORM OF (3R,4R)-(1-BENZYL-4-METHYL-PIPERIDIN-3-YL)-METHYL- (7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)-AMINE

Provided are processes for the preparation of a solid state form of (3R,4R)-(1-Benzyl-4-methyl- piperidin-3-yl)-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine.

N 5 g of (3R,4R)-(1-Benzyl-4-methyl-piperidin-3-yl)-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine were suspended in 20 mL of EtOH. After 2 h at ambient temperature, the suspension was cooled down to 2ºC in 1 h. After filtering and washing the cake with 20 mL of EtOH, the product was obtained in 74.1% yield.

Example 2

5 g of (3R,4R)-(1-Benzyl-4-methyl-piperidin-3-yl)-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine were suspended in 10 mL of EtOH. The suspension was heated up to reflux obtaining total dissolution. Then, 50 mL of heptane were added keeping the reflux. Afterwards, the solution was cooled down slowly to 2 ºC. After 1 h at 2 ºC, the suspension was filtered and washed with 20 mL of EtOH /Heptane 1:5. The product was obtained in 65.5%.

In both cases the same crystalline form was obtained:

Diffractogram:

Figure 1. XRPD of sample (3R,4R)-(1-Benzyl-4-methyl-piperidin-3-yl)-methyl-(7H- pyrrolo[2,3-d]pyrimidin-4-yl)-amine

1

N

N

N NH

Example 1



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XRPD Peak list

Peak Number Pos. [°2Th.] d-spacing [Å] Height [cts] Rel. Int. [%]

1 13,08 6,76 322 7,4

2 13,77 6,43 3147 72,5

13,96 6,34 4340 100,0

14,49 6,11 216 5,0

14,80 5,98 574 13,2

15,42 5,74 465 10,7

15,67 5,65 984 22,7

15,84...