Methyl vinyl sulfone → HCID 24831310, compound

HRID 1435119Notes

Reaction equation

HRID 1435119 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[C:6]([F:15])[CH:5]=[CH:4][C:3]=1[C@H:16]([O:18][C:19]1[CH:23]=[C:22]([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33]4[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[S:21][C:20]=1[C:39]([NH2:41])=[O:40])[CH3:17].[CH:42]([S:44]([CH3:47])(=[O:46])=[O:45])=[CH2:43]>>[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:43][CH2:42][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:11][CH2:10]2)=[C:6]([F:15])[CH:5]=[CH:4][C:3]=1[C@H:16]([O:18][C:19]1[CH:23]=[C:22]([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33]4[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[S:21][C:20]=1[C:39]([NH2:41])=[O:40])[CH3:17]

Participants

3

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 24831152HCID 24831152, compound

Product 1

HCID 24831310HCID 24831310, compoundYield 79%

Procedure

3-({(1R)-1-[2-chloro-4-fluoro-3-(4-piperidinyloxy)phenyl]ethyl}oxy)-5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxamide (Example 33, Step A, 80 mg, 0.13 mmol) and methyl vinyl sulfone (13 μL, 0.15 mmol) were coupled using a procedure analogous to Example 23 to give 72 mg of the title compound (79%). 1H NMR (400 MHz, d6-DMSO) δ 8.52 (s, 1H), 8.17 (s, 1H), 7.95 (s, 1H), 7.91 (s, 1H), 7.79 (br s, 1H), 7.56 (m, 2H), 7.45-7.35 (m, 2H), 7.13 (s, 1H), 7.08 (br s, 1H), 5.94 (m, 1H), 4.13 (m, 1H), 3.85 (s, 3H), 3.17 (t, J=6.2 Hz, 2H), 2.97 (s, 3H), 2.69-2.58 (m, 4H), 2.07 (m, 2H), 1.81-1.66 (m, 7H). HRMS calculated [M+H]+ C32H35ClFN6O5S2 701.17774, found 701.17740.

Sources & evidence

ORD record
ord-a358428eb6fb4f1097ead80cb13709a8
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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