1-(2,2,2-Trifluoroethyl)pyrrolidinone → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N5-[1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]pyrimidine-4,5-diamine

HRID 510065Notes

Reaction equation

HRID 510065 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][C:27]([F:36])([F:35])[CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O>>[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]([NH:21][CH:31]3[CH2:32][CH2:33][N:29]([CH2:28][C:27]([F:36])([F:35])[F:26])[CH2:30]3)=[CH:16][N:15]=2)=[N:6]1

Participants

3

Reactant 2

HCID 210762201-(2,2,2-Trifluoroethyl)pyrrolidinoneHCID 219348172-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamine

Product 1

HCID 666137772-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N5-[1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]pyrimidine-4,5-diamine

Procedure

400 mg (1.193 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-(2,2,2-trifluoroethyl)pyrrolidinone. After purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient), this gave 482 mg of the title compound (83% of theory).

Workup

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

Sources & evidence

ORD record
ord-b100059f685240d0b6eb835f8118c76a
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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