1-Hydroxybenzotriazole → HCID 66755035, compound

HRID 1643975Notes

Reaction equation

HRID 1643975 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9](=[O:22])[N:8]([CH:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24](O)=[O:25])[C:7]=2[CH:33]=1)#[N:2].ON1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2N=N1.[NH:44]=[C:45]=N.[CH3:47][CH2:48][NH+:49]([CH2:52][CH3:53])[CH2:50][CH3:51].[CH3:54][CH2:55][NH+:56](CC)CC.C([O-])([O-])=O>C(Cl)Cl>[CH2:45]([N:44]1[CH2:51][CH2:50][N:49]([C@H:52]2[CH2:54][CH2:55][N:56]([C:24](=[O:25])[CH:23]([N:8]3[C:7]4[CH:33]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=4[N:10]([S:11]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)(=[O:12])=[O:13])[C:9]3=[O:22])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:53]2)[CH2:48][CH2:47]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 24900959[6-Cyano-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]phenylacetic acid

Product 1

HCID 66755035HCID 66755035, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-cyano-3-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-phenyl-acetic acid XIIIc (200 mg, 0.43 mmol), 1-hydroxybenzotriazole (88 mg, 0.65 mmol) and PS-carbodiimide resin (Argonaut; 1.18 mmol/g; 439 mg, 0.52 mmol) in CH2Cl2 (5 mL) was agitated for 10 min at room temperature. Then, 1-benzyl-4-(S)-pyrrolidin-3-yl-piperazine (166 mg, 0.47 mmol) was added and the reaction mixture was agitated at room temperature overnight. To this mixture MP-carbonate resin (Argonaut; 2.69 mmol/g; 481 mg, 1.29 mmol) was added and the reaction mixture was agitated for another 2 hours, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent to afford 3-{2-[(S)-3-(4-benzyl-piperazin-1-yl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-1-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (135 mg, 45%) as a white solid.

Workup

  1. stirringthe reaction mixture was agitated at room temperature overnight
  2. stirringthe reaction mixture was agitated for another 2 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-105643e99b9f40c29e9da733ddfd6f71
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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