Methyl vinyl sulfone → HCID 24830829, compound

HRID 1435118Notes

Reaction equation

HRID 1435118 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]2[N:6]([C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[C:11]([O:17][C@@H:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[C:21]=4[Cl:33])[CH3:19])[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[CH:36]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH2:37]>C1COCC1>[Cl:1][C:2]1[CH:35]=[CH:34][C:5]2[N:6]([C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[C:11]([O:17][C@@H:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]5[CH2:32][CH2:31][N:30]([CH2:37][CH2:36][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:29][CH2:28]5)[C:21]=4[Cl:33])[CH3:19])[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 24830358HCID 24830358, compound2×

Product 1

HCID 24830829HCID 24830829, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-{5-chloro-1H-benzimidazol-1-yl)-3-({(1R)-1-[2-chloro-3-(4-piperidinyloxy)phenyl]ethyl}oxy}-2-thiophenecarboxamide (Intermediate 12, 112 mg, 0.21 mmol) and methyl vinyl sulfone (22 μL, 0.25 mmol) in 2 mL THF were stirred until the starting material was consumed. The reaction was concentrated onto silica gel and purified by flash column chromatography to give 105 mg of the title compound (78%). 1H NMR (400 MHz, d6-DMSO) δ 8.61 (s, 1H), 7.83 (m, 1H), 7.80 (br s, 1H), 7.51 (d, J=8.8 Hz, 1H), 7.36-7.29 (m, 2H), 7.20-7.13 (m, 3H), 7.08 (br s, 1H), 5.95 (m, 1H), 4.48 (m, 1H), 3.25-3.21 (m, 2H), 2.99 (s, 3H), 2.67-2.64 (m, 4H), 2.29 (m, 2H), 1.85 (m, 2H), 1.68 (d, J=6.0 Hz, 3H), 1.62 (m, 2H). HRMS calculated [M+H]+ C28H31Cl2N4O5S2 637.1113, found 637.1120.

Workup

  1. customwas consumed
  2. concentrationThe reaction was concentrated onto silica gel
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-adedf72e6f6d4dc7b5bcd518fb677073
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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