2-Thiopheneacetyl chloride → HCID 57737206, compound

HRID 1157580Notes

Reaction equation

HRID 1157580 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[CH:26]=4)[N:19]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43](Cl)=[O:44]>>[CH3:35][N:34]([CH3:36])[CH2:33][CH2:32][O:31][C:27]1[CH:26]=[C:25]([NH:24][C:20]2[N:19]=[C:18]([C:17]3[C:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][C:43](=[O:44])[CH2:42][C:38]5[S:37][CH:41]=[CH:40][CH:39]=5)[CH:3]=4)=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=34)[CH:23]=[CH:22][N:21]=2)[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 59511402HCID 59511402, compound

Product 1

HCID 57737206HCID 57737206, compoundYield 37%

Procedure

The title compound was prepared 4-[2-(3-amino-4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine and 2-thiopheneacetyl chloride using the acylation conditions described in Example 36, Step H to generate, after HPLC purification, the desired product as a TFA salt in 37% yield. 1H NMR (400 MHz, d6-DMSO) δ 10.15 (s, 1H), 9.62 (s, 1H), 8.85 (d, J=6.8 Hz, 1H), 8.49 (d, J=8.7 Hz, 1H), 8.27 (d, J=5.5 Hz, 2H), 7.61 (s, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.30-7.39 (m, 3H), 7.19 (t, J=8.0 Hz, 2H), 7.13 (t, J=6.9 Hz, 2H), 6.96-6.98 (m, 1H), 6.60 (d, J=6.1 Hz, 1H), 6.55 (d, J=5.3 Hz, 1H), 4.25-4.26 (m, 2H), 3.99 (s, 2H), 3.50 (m, 2H), 2.85 (s, 6H). ES-LC/MS m/z=608 [M+H]+.

Workup

  1. customafter HPLC purification

Sources & evidence

ORD record
ord-4dbc9bd147744873a64892db69b4bf47
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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