2-Thiopheneacetyl chloride → HCID 57737153, compound

HRID 1157606Notes

Reaction equation

HRID 1157606 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]([O:30][CH3:31])=[C:26]([N:32]5[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH2:34][CH2:33]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:44]1[CH:48]=[CH:47][CH:46]=[C:45]1[CH2:49][C:50](Cl)=[O:51]>>[CH3:31][O: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:50](=[O:51])[CH2:49][C:45]5[S:44][CH:48]=[CH:47][CH:46]=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[N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][S:40]([CH3:43])(=[O:41])=[O:42])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737253HCID 57737253, compound

Product 1

HCID 57737153HCID 57737153, compoundYield 47%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-(methyloxy)-3-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}phenyl)-2-pyrimidinamine using 2-thienylacetyl chloride as described in Example 10, Step E to give a light brown solid in 47% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.5 (m, 4H) 2.7 (m, 3H) 2.9 (m, 4H) 3.0 (s, 3H) 3.7 (s, 3H) 3.9 (s, 2H) 6.4 (d, J=5.1 Hz, 1H) 6.8 (d, J=9.1 Hz, 1H) 7.0 (d, J=4.6 Hz, 2H) 7.1 (t, J=6.6 Hz, 1H) 7.3 (m, 3H) 7.4 (d, J=10.4 Hz, 1H) 7.4 (m, 2H) 7.7 (d, J=8.1 Hz, 1H) 7.9 (s, 1H) 8.2 (d, J=5.5 Hz, 1H) 8.8 (d, J=7.0 Hz, 1H) 9.3 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 723 [M+H]+.

Workup

  1. customto give a light brown solid in 47% yield

Sources & evidence

ORD record
ord-bcedef1a874f4efbaf32804c389365e0
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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