Water → HCID 22714359, compound

HRID 1582211Notes

Reaction equation

HRID 1582211 reaction equation
[C:1](Cl)(=O)[C:2]1C=CC=C[CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)([OH:24])[C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)=[CH:13][C:12]=1[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)=[O:33].N1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[OH2:47]>C(Cl)Cl>[Cl:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[C:32]([C:12]1[CH:13]=[C:14]([C:17]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)([OH:24])[C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)[CH:15]=[CH:16][C:11]=1[NH:10][C:42](=[O:47])[CH2:43][C:44]1[CH:3]=[CH:2][CH:1]=[CH:46][CH:45]=1)=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22714353HCID 22714353, compound

Product 1

HCID 22714359HCID 22714359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of benzoyl chloride (3.1 ml) in DCM (25 ml) was added dropwise at room temperature to a solution of interm. (6-d) (7 g) and pyridine (5 ml) in DCM (70 ml). The mixture was stirred at room temperature for 45 minutes. Water was added and the mixture was decanted. The organic layer was dried, filtered and the solvent was evaporated, yielding 8.8 g of (±)-N-[2-(3-chlorobenzoyl)-4-[(4-chlorophenyl)-hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl]benzeneacetamide (interm. 7). The product was used without further purification.

Workup

  1. additionwas added dropwise at room temperature to a solution of interm
  2. customthe mixture was decanted
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-98538fc982b84e0db6b47f09a9628d7f
Source dataset
uspto-grants-2004_05
Patent number
US06734194B2

Reaction notes

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