2-Thiopheneacetyl chloride → HCID 57737187, compound

HRID 1157559Notes

Reaction equation

HRID 1157559 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][N:33]([CH2:36]C)[CH2:34]C)[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:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][C:44](Cl)=[O:45]>>[CH3:34][N:33]([CH3:36])[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:44](=[O:45])[CH2:43][C:39]5[S:38][CH:42]=[CH:41][CH:40]=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 57737240HCID 57737240, compound

Product 1

HCID 57737187HCID 57737187, compoundYield 57%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(diethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine using acylation with 2-thienylacetyl chloride as described in Example 10, Step E to yield a light brown solid in 57% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.8 (s, 5H) 3.8 (d, J=0.9 Hz, 3H) 3.9 (s, 1H) 4.2 (s, 1H) 6.5 (d, J=5.3 Hz, 1H) 6.6 (s, 1H) 6.9 (m, 6H) 7.1 (s, 3H) 7.2 (s, 1H) 7.4 (m, 1H) 7.6 (s, 1H) 7.7 (s, 1H) 7.9 (s, 1H) 8.2 (d, J=5.5 Hz, 1H) 8.5 (s, 1H) 8.8 (m, 1H) 9.6 (s, 1H) 10.4 (s, 1H). ES-LC/MS m/z 590 [M+H]+.

Workup

  1. customto yield a light brown solid in 57% yield

Sources & evidence

ORD record
ord-2faa6693c9d1429f81d35ef68aaa2beb
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…