(5-Bromopyridin-2-yl)acetic acid → N-(5-{[2-amino-7-(1-hydroxy-2-methylpropan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)-2-(5-bromopyridin-2-yl)acetamide

HRID 82112Notes

Reaction equation

HRID 82112 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([NH2:19])[CH:18]=3)=[O:12])=[CH:9][N:8]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])[C:6]=2[N:7]=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33](O)=[O:34])=[N:30][CH:31]=1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([C:13]3[CH:18]=[C:17]([NH:19][C:33](=[O:34])[CH2:32][C:29]4[CH:28]=[CH:27][C:26]([Br:25])=[CH:31][N:30]=4)[CH:16]=[N:15][CH:14]=3)=[O:12])=[CH:9][N:8]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 46238459(5-Bromopyridin-2-yl)acetic acidHCID 70817292[2-amino-7-(2-hydroxy-1,1-dimethylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl](5-aminopyridin-3-yl)methanone

Product 1

HCID 70817529N-(5-{[2-amino-7-(1-hydroxy-2-methylpropan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)-2-(5-bromopyridin-2-yl)acetamide

Procedure

The title compound was prepared according to the method described for Example 34 at 50° C. using [2-amino-7-(2-hydroxy-1,1-dimethylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl](5-aminopyridin-3-yl)methanone (Preparation 48) and (5-bromopyridin-2-yl)acetic acid to afford the title compound as a yellow solid in 60% yield, 75 mg. LCMS (System 10): Rt=2.69 min; m/z 524 [M+H]+

Workup

  1. customThe title compound was prepared
  2. customdescribed for Example 34 at 50° C.

Sources & evidence

ORD record
ord-a5e0045cb3d24c40800d6fec8abbcdf0
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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