2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamine → N5-[1-(2,2-Difluoroethyl)piperidin-4-yl]-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine

HRID 510066Notes

Reaction equation

HRID 510066 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][N:15]=2)=[N:6]1.[F:26][CH:27]([F:36])[CH2:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1>>[F:26][CH:27]([F:36])[CH2:28][N:29]1[CH2:34][CH2:33][CH:32]([NH:21][C:17]2[C:18]([NH2:20])=[N:19][C:14]([C:7]3[C:8]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[N:5]([CH2:4][C:3]4[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=4[F:1])[N:6]=3)=[N:15][CH:16]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 219348172-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamineHCID 470027111-(2,2-Difluoroethyl)piperidin-4-one

Product 1

HCID 86720048N5-[1-(2,2-Difluoroethyl)piperidin-4-yl]-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine

Procedure

200 mg (0.596 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine (synthesis described in US2004/67937; Example V) were reacted in analogy to the method in example 88A with 1-(2,2-difluoroethyl)piperidin-4-one. After purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient), this gave 219 mg of the title compound (76% of theory).

Workup

  1. customAfter purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-8574c7b2925840848f9d7891311c1819
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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