2-Thiopheneacetyl chloride → HCID 57737184, compound

HRID 1157579Notes

Reaction equation

HRID 1157579 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:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[CH2:30][CH:29]([N:34]([CH3:36])[CH3:35])[CH2:28]5)[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])[CH:29]1[CH2:28][C:27]2[C:31](=[CH:32][CH:33]=[C:25]([NH:24][C:20]3[N:19]=[C:18]([C:17]4[C:9]([C:4]5[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][C:43](=[O:44])[CH2:42][C:38]6[S:37][CH:41]=[CH:40][CH:39]=6)[CH:3]=5)=[N:10][N:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=45)[CH:23]=[CH:22][N:21]=3)[CH:26]=2)[CH2:30]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 59511395HCID 59511395, compound

Product 1

HCID 57737184HCID 57737184, compound

Procedure

The title compound was prepared from {4-[2-(3-amino-4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]amine and 2-thiopheneacetyl chloride using acylation conditions described in Example 36, Step H to generate the desired product in 76% yield. 1H NMR (400 MHz, d6-DMSO) δ 10.14 (s, 1H), 9.42 (s, 1H), 8.83 (d, J=6.9 Hz, 1H), 8.42 (d, J=8.7 Hz, 1H), 8.29 (d, J=6.6 Hz, 1H), 8.25 (d, J=5.4 Hz, 1H), 7.61 (s, 1H), 7.35-7.47 (m, 5H), 7.03-7.13 (m, 4H), 6.52 (d, J=5.4 Hz, 1H), 3.99 (s, 2H), 2.87-2.99 (m, 3H), 2.66-2.72 (m, 2H), 2.21 (s, 6H). ES-LC/MS m/z=604 [M+H]+.

Sources & evidence

ORD record
ord-77ee66c421fc45e4ab200eb5e67a61c6
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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