(Pyrimidin-5-yl)boronic acid → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyrimidin-5-yl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184834Notes

Reaction equation

HRID 1184834 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:30]=[N:31][CH:32]=C[CH:34]=4)[N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[N:40]1C=C(B(O)O)C=NC=1>>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[N:40][CH:32]=[N:31][CH:30]=4)[N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86680167N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide

Product 1

HCID 86680168N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyrimidin-5-yl)thieno[2,3-b]pyrazine-6-carboxamideYield 7%

Procedure

Preparation analogous to the synthesis of 25h by using pyrimidine-5-boronic acid (1.5 eq). Purified by HPLC to give the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyrimidin-5-yl)thieno[2,3-b]pyrazine-6-carboxamide 25j (2 mg, 7%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.28 (s, 3H), 7.33 (d, J=8.6 Hz, 1H), 7.58-7.67 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.9 (d, J=1.9 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 8.06 (s, 1H), 8.63 (br s, 1H), 9.37 (s, 1H), 9.51 (s, 1H), 9.61 (s, 2H), 10.38 (br s, 1H). (m/z)=534 (M+H)+.

Workup

  1. customPreparation
  2. customPurified by HPLC

Sources & evidence

ORD record
ord-431599cdd324458199a5db141b526a85
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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