Diisopropylethylamine → 2-(5-bromopyridin-2-yl)-N-(5-{[7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)acetamide

HRID 82113Notes

Reaction equation

HRID 82113 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[CH:12]=[C:13]([C:17]([C:19]2[C:27]3[CH:26]=[N:25][CH:24]=[N:23][C:22]=3[N:21]([CH:28]([CH3:30])[CH3:29])[CH:20]=2)=[O:18])[CH:14]=[N:15][CH:16]=1.[Br:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][C:39](O)=[O:40])=[N:36][CH:37]=1>>[Br:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][C:39]([NH:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13]([C:17]([C:19]3[C:27]4[CH:26]=[N:25][CH:24]=[N:23][C:22]=4[N:21]([CH:28]([CH3:30])[CH3:29])[CH:20]=3)=[O:18])[CH:12]=2)=[O:40])=[N:36][CH:37]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 46238459(5-Bromopyridin-2-yl)acetic acidHCID 70817456(5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

Product 1

HCID 708176032-(5-bromopyridin-2-yl)-N-(5-{[7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)acetamide

Procedure

The title compound was prepared according to the method described for Example 1 with DIPEA using (5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (Preparation 95) and (5-bromopyridin-2-yl)acetic acid to afford the title compound as a yellow solid in 45% yield, 75 mg. LCMS (System 9): Rt=2.97 min; m/z 479 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-894455204e944fd4b23859a26800d88c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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