Dichloromethane → HCID 66755118, compound

HRID 1631996Notes

Reaction equation

HRID 1631996 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:4]=2[N:3]1[CH:13]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:14](=[O:29])[N:15]1[CH2:19][CH2:18][C@H:17]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]2)[CH2:16]1.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[S:44](Cl)(=[O:46])=[O:45].C(Cl)Cl>CN(C1C=CN=CC=1)C>[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[S:44]([N:6]1[C:5]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:4]=2[N:3]([CH:13]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:14](=[O:29])[N:15]2[CH2:19][CH2:18][C@H:17]([N:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]3)[CH2:16]2)[C:2]1=[O:1])(=[O:46])=[O:45]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 37458512-Methoxybenzenesulfonyl ChlorideHCID 66754796HCID 66754796, compound

Product 1

HCID 66755118HCID 66755118, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 2-oxo-3-{2-oxo-1-phenyl-2-[(S)-3-(4-propyl-piperazin-1-yl)-pyrrolidin-1-yl]-ethyl}-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (70 mg, 0.15 mmol), DMAP (catalytic amount) and 2-methoxybenzenesulfonyl chloride (37 mg, 0.18 mmol) in CH2Cl2 (3 mL) SilicaBond-diethylamine resin (Silicycle; 1.04 mmol/g; 570 mg, 0.59 mmol) was added. The reaction mixture was agitated at room temperature for 24 hours, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 4% methanol in CH2Cl2 as eluent to afford 1-(2-methoxy-benzenesulfonyl)-2-oxo-3-{2-oxo-1-phenyl-2-[(S)-3-(4-propyl-piperazin-1-yl)-pyrrolidin-1-yl]ethyl}-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (55 mg, 57%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel using 4% methanol in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-a94ae9d051db4373b5b0d27cf34f1a8f
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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