2-Thiopheneacetyl chloride → HCID 57737249, compound

HRID 1157601Notes

Reaction equation

HRID 1157601 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]([CH3:41])[CH:35]5[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]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:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[CH2:47][C:48](Cl)=[O:49]>>[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:48](=[O:49])[CH2:47][C:43]5[S:42][CH:46]=[CH:45][CH:44]=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]([CH3:41])[CH:35]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737191HCID 57737191, compound

Product 1

HCID 57737249HCID 57737249, compoundYield 55%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[4-chloro-3-({2-[methyl(1-methyl-3-pyrrolidinyl)amino]ethyl}oxy)phenyl]-2-pyrimidinamine using 2-thienylacetyl chloride as described in Example 10, Step E to give a brown solid in 55% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.7 (s, 2H) 2.8 (m, 5H) 3.0 (d, J=14.5 Hz, 4H) 3.1 (s, 2H) 3.8 (s, 1H) 3.9 (s, 1H) 3.9 (s, 2H) 4.0 (s, 1H) 6.5 (d, J=5.3 Hz, 1H) 6.9 (s, 2H) 6.9 (s, 3H) 7.1 (m, 2H) 7.2 (m, 3H) 7.4 (m, 2H) 7.5 (d, J=8.6 Hz, 1H) 7.7 (d, J=20.0 Hz, 1H) 7.9 (s, 1H) 8.3 (d, J=5.1 Hz, 1H) 8.8 (d, J=6.4 Hz, 1H) 9.7 (s, 1H) 10.4 (s, 1H). ES-LC/MS m/z 693 [M+H]+.

Workup

  1. customto give a brown solid in 55% yield

Sources & evidence

ORD record
ord-faf9de0967944091b4d0ba21af3cf889
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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