Benzoyl chloride → HCID 86745955, compound

HRID 893601Notes

Reaction equation

HRID 893601 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([Cl:27])[N:20]=[C:19]2[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=1)(=[O:4])=[O:3].[C:32](Cl)(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH2:32]([NH:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][N:18]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([Cl:27])[N:20]=[C:19]2[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:15][CH:16]=1)(=[O:4])=[O:3])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 10253779HCID 10253779, compound

Product 1

HCID 86745955HCID 86745955, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-((2'-(aminosulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid, methyl ester (67.0 mg, 0.145 mmol) in pyridine (1.0 ml) under nitrogen at room temperature was added benzoyl chloride (168 μl, 1.45 mmol) dropwise. The pale orange solution was stirred at room temperature for 12 hours then saturated sodium bicarbonate solution added. The mixture was extracted four times with ethyl acetate. The compound organic phase was washed with water, twice with saturated copper sulfate solution, water, brine and dried (magnesium sulfate). The solvent was removed in vacuo and the residue chromatographed (silica gel, 2% methanolmethylene chloride) to give 1-((2'-((benzylamino)sulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid, methyl ester (63.4 mg, 77%) as a white solid; 1H NMR (300 MHz, CD3OD) δ8.30 (dd, J=7.7, 1.7 Hz, 1H), 7.65-7.42 (m, 5H), 7.40-7.30 (m, 2H), 7.29-7.18 (m, 3H), 6.90 (d, J=8.2 Hz, 2H), 5.54 (s, 2H), 3.84 (s, 3H), 2.62 (t, J=7.8 Hz, 2H), 1.64 (quin, J=7.8 Hz, 2H), 1.32 (apparent sext, 2H), 0.87 (t, J=7.3 Hz, 3H); FAB-MS: 568 and 566 (M+H).

Workup

  1. extractionThe mixture was extracted four times with ethyl acetate
  2. washThe compound organic phase was washed with water, twice with saturated copper sulfate solution, water, brine
  3. dry with materialdried (magnesium sulfate)
  4. customThe solvent was removed in vacuo
  5. customthe residue chromatographed (silica gel, 2% methanolmethylene chloride)

Sources & evidence

ORD record
ord-e8f969ee22d2446d94b4655f5efddaa6
Source dataset
uspto-grants-1992_06
Patent number
US05126342

Reaction notes

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