2-Thiopheneacetyl chloride → HCID 57737152, compound

HRID 1157555Notes

Reaction equation

HRID 1157555 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]5[CH2:39][CH2:38][O: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:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[CH2:45][C:46](Cl)=[O:47]>>[N:34]1([CH2:33][CH2:32][CH2:31][O:30][C:26]2[CH:25]=[C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:46](=[O:47])[CH2:45][C:41]6[S:40][CH:44]=[CH:43][CH:42]=6)[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)[CH:29]=[CH:28][CH:27]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737247HCID 57737247, compound

Product 1

HCID 57737152HCID 57737152, compoundYield 37%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[3-(4-morpholinyl)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 37% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (d, J=1.1 Hz, 2H) 2.3 (s, 6H) 3.5 (d, J=4.6 Hz, 4H) 3.9 (s, 2H) 3.9 (m, 2H) 6.5 (m, 2H) 7.0 (m, 2H) 7.1 (m, 2H) 7.3 (dt, J=7.6, 1.4 Hz, 2H) 7.4 (m, 3H) 7.5 (t, J=2.1 Hz, 1H) 7.7 (d, J=1.8 Hz, 1H) 7.9 (t, J=1.8 Hz, 1H) 8.2 (d, J=5.3 Hz, 1H) 8.5 (d, J=8.6 Hz, 1H) 8.8 (m, 1H) 9.5 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 646 [M+H]+.

Workup

  1. customto yield a light brown solid in 37% yield

Sources & evidence

ORD record
ord-27b39854420445e9973e176a07cbacd0
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…