2-Thiopheneacetyl chloride → HCID 57737196, compound

HRID 1157556Notes

Reaction equation

HRID 1157556 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][CH:27]=[C:26]([O:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[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:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43](Cl)=[O:44]>>[CH3:36][N:34]([CH3:35])[CH2:33][CH2:32][CH2:31][O:30][C:26]1[CH:25]=[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:43](=[O:44])[CH2:42][C:38]5[S:37][CH:41]=[CH:40][CH:39]=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:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 59511423HCID 59511423, compound

Product 1

HCID 57737196HCID 57737196, compoundYield 48%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[3-(dimethylamino)propyl]oxy}phenyl)-2-pyrimidinamine using acylation with 2-thienylacetyl chloride as described in Example 10, Step E to yield a light brown solid in 48% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (s, 2H) 2.1 (s, 6H) 2.3 (s, 2H) 3.9 (s, 2H) 3.9 (d, J=6.2 Hz, 2H) 6.5 (m, 2H) 7.0 (m, 2H) 7.1 (m, 2H) 7.3 (s, 2H) 7.4 (m, 2H) 7.5 (m, 2H) 7.7 (m, 1H) 7.9 (d, J=2.2 Hz, 1H) 8.2 (d, J=5.3 Hz, 1H) 8.5 (s, 1H) 8.8 (d, J=7.0 Hz, 1H) 9.5 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 604 [M+H]+.

Workup

  1. customto yield a light brown solid in 48% yield

Sources & evidence

ORD record
ord-988e1627dc7149268c82710a3732dfaf
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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