2-Thiopheneacetyl chloride → HCID 57737157, compound

HRID 1157600Notes

Reaction equation

HRID 1157600 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]([CH3:36])[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]>>[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: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:25][C:26]=1[O:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737185HCID 57737185, compound

Product 1

HCID 57737157HCID 57737157, compoundYield 70%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(dimethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine using 2-thienylacetyl chloride as described in Example 10, Step E to give a yellow solid in 70% yield. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.2 (s, 6H) 2.6 (t, J=5.8 Hz, 2H) 3.9 (s, 2H) 4.0 (t, J=6.0 Hz, 2H) 6.6 (d, J=5.2 Hz, 1H) 7.0 (d, J=4.2 Hz, 2H) 7.2 (m, 1H) 7.3 (m, 1H) 7.4 (m, 2H) 7.5 (s, 1H) 7.6 (s, 1H) 7.8 (m, 2H) 7.9 (s, 1H) 8.3 (d, J=5.2 Hz, 1H) 8.5 (d, J=9.7 Hz, 1H) 8.9 (d, J=6.7 Hz, 2H) 9.7 (s, 1H) 10.4 (s, 1H). ES-LC/MS m/z 624 [M+H]+.

Workup

  1. customto give a yellow solid in 70% yield

Sources & evidence

ORD record
ord-4701ad24ac4841a9b8ae623f56491858
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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