Benzenesulfonyl chloride → HCID 58653660, compound

HRID 1676089Notes

Reaction equation

HRID 1676089 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([CH:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:16]=3)[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:8][C:4]=2[CH:3]=1.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)C(C)C)(C)C>ClCCl>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:20][C:15]([CH:9]([N:6]2[C:5]3[CH:27]=[CH:28][C:2]([NH:1][S:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:37])=[O:36])=[CH:3][C:4]=3[N:8]=[CH:7]2)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58653671HCID 58653671, compound

Product 1

HCID 58653660HCID 58653660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(5-amino-1H-benzimidazol-1-yl)-3-(1,1′-biphenyl)-4-ylpropanoate (15 mg, 40 μmol) in dichloromethane (500 μL) was added benzenesulfonyl chloride (6.0 μL, 47 μmol) and N,N-diisopropylethylamine (8.0 μL, 46 μmol). The solution was stirred at room temperature for 48 hours, and was then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (96:4), to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=5.50 min, MH+ 513].

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and methanol (96:4)

Sources & evidence

ORD record
ord-d5d2490db9ec43f29aed1c800c881cc7
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

Loading…