2-Thiopheneacetyl chloride → N-[3-(3-{2-[(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide

HRID 1157599Notes

Reaction equation

HRID 1157599 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([O:31][CH2:32][CH2:33][N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][C:45](Cl)=[O:46]>>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:19]2[N:18]=[C:17]([C:16]3[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:45](=[O:46])[CH2:44][C:40]5[S:39][CH:43]=[CH:42][CH:41]=5)[CH:7]=[CH:6][CH:5]=4)=[N:9][N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=34)[CH:22]=[CH:21][N:20]=2)=[CH:25][C:26]=1[O:31][CH2:32][CH2:33][N:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 577372284-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamine

Product 1

HCID 57737186N-[3-(3-{2-[(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamideYield 71%

Procedure

The title compound was prepared from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamine and 2-thiopheneacetyl chloride using acylation conditions described in Example 1, Step F, and purification via column chromatography using a 0-20% gradient of EtOAc/MeOH w/NH4OH to generate the product in 71% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.7 (s, 4H) 3.8 (s, 3H) 4.0 (s, 3H) 6.5 (s, 1H) 6.9 (d, J=4.4 Hz, 2H) 7.1 (t, J=6.9 Hz, 2H) 7.2 (t, J=9.0 Hz, 2H) 7.4 (m, 3H) 7.5 (m, 2H) 7.7 (s, 2H) 7.9 (s, 1H) 8.2 (d, J=0.9 Hz, 1H) 8.4 (s, 1H) 8.8 (d, J=1.3 Hz, 1H) 9.7 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 650 [M+H]+.

Workup

  1. customdescribed in Example 1, Step F, and purification via column chromatography

Sources & evidence

ORD record
ord-ebcb78249bbb4c5aa8c5c9917b494e0e
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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