2-Thiopheneacetyl chloride → HCID 57737175, compound

HRID 1157578Notes

Reaction equation

HRID 1157578 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]([CH2:31][N:32]([CH3:34])[CH3:33])[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:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[CH2:40][C:41](Cl)=[O:42]>C1COCC1.CCOC(C)=O>[CH3:33][N:32]([CH2:31][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:41](=[O:42])[CH2:40][C:36]5[S:35][CH:39]=[CH:38][CH:37]=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)[CH3:34]

Participants

5

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737189HCID 57737189, compound

Product 1

HCID 57737175HCID 57737175, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-[2-(3-amino-4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-{3-[(dimethylamino)methyl]phenyl}-2-pyrimidinamine (58 mg, 0.13 mmol) in THF (3 mL) was added TEA (27 μL, 0.19 mmol) and 2-thiopheneacetyl chloride (17 μL, 0.13 mmol). After 20 h, the reaction mixture was diluted with EtOAc (20 mL), adsorbed onto silica gel, and purified by column chromatography to give the title compound (58 mg, 77% yield). 1H NMR (400 MHz, d6-DMSO) 610.15 (s, 1H), 9.54 (s, 1H), 8.83 (d, J=7.0 Hz, 1H), 8.48 (d, J=8.8 Hz, 1H), 8.26-8.29 (m, 2H), 7.69 (s, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.47 (t, J=7.9 Hz, 1H), 7.36-7.39 (m, 2H), 7.18 (t, J=7.8 Hz, 1H), 7.13 (t, J=6.9 Hz), 6.96-6.98 (m, 2H), 6.87 (d, J=7.1 Hz, 1H), 6.52 (d, J=5.3 Hz, 1H), 3.99 (s, 2H), 3.32 (s, 2H), 2.15 (s, 6H). ES-LC/MS m/z=578 [M+H]+.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-38b9814cda1e4aff9ef1ef15e31b035c
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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