2-Thiopheneacetyl chloride → HCID 57737258, compound

HRID 1157558Notes

Reaction equation

HRID 1157558 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][CH3:37])[CH2:34][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:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][C:44](Cl)=[O:45]>>[CH2:34]([N:33]([CH2:36][CH3:37])[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)[CH3:35]

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737240HCID 57737240, compound

Product 1

HCID 57737258HCID 57737258, compoundYield 49%

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 49% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (t, J=7.2 Hz, 6H) 3.2 (s, 4H) 3.5 (s, 2H) 3.9 (s, 2H) 4.3 (s, 2H) 6.5 (d, J=5.3 Hz, 1H) 6.6 (s, 1H) 7.0 (m, 2H) 7.1 (d, J=1.5 Hz, 1H) 7.3 (d, J=5.1 Hz, 1H) 7.4 (m, 2H) 7.5 (m, 1H) 7.6 (s, 1H) 7.7 (s, 1H) 7.9 (s, 1H) 8.2 (d, J=5.3 Hz, 1H) 8.5 (s, 1H) 8.8 (d, J=7.0 Hz, 1H) 9.6 (s, 2H) 10.4 (s, 1H). ES-LC/MS m/z 618 [M+H]+.

Workup

  1. customto yield a light brown solid in 49% yield

Sources & evidence

ORD record
ord-4bea31dd3d424dfdb2365a48ffda5a07
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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