2-Thiopheneacetyl chloride → HCID 16122935, compound

HRID 1157553Notes

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]5[CH2:37][CH2:36][CH2:35][CH2:34]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:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH2:43][C:44](Cl)=[O:45]>>[N:33]1([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:44](=[O:45])[CH2:43][C:39]6[S:38][CH:42]=[CH:41][CH:40]=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)[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

Reactant 2

HCID 1623622-Thiopheneacetyl chloride

HCID 59511429HCID 59511429, compound

Product 1

HCID 16122935HCID 16122935, compoundYield 44%

Procedure

The title compound was prepared from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamine and 2-thiopheneacetyl chloride using acylation conditions described in Example 1, Step F, and purification via column chromatography using a 0-20% gradient of EtOAc/MeOH w/NH4OH to generate the product in 44% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.6 (s, 4H) 2.7 (s, 3H) 3.8 (s, 2H) 4.0 (t, J=6.0 Hz, 2H) 6.5 (m, 2H) 6.9 (m, 2H) 7.1 (m, 3H) 7.2 (m, 2H) 7.4 (m, 2H) 7.4 (m, 1H) 7.5 (t, J=2.3 Hz, 1H) 7.7 (m, 1H) 7.9 (d, J=1.8 Hz, 1H) 8.2 (d, J=5.3 Hz, 1H) 8.5 (s, 1H) 8.8 (d, J=7.0 Hz, 1H) 9.5 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 616 [M+H]+.

Workup

customdescribed in Example 1, Step F, and purification via column chromatography

Sources & evidence

ORD record: ord-729e951cfb3246d08699a9fc683f66a4
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807673B2

Reaction notes

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