Diethyl Pyrocarbonate → 2-Methyl-N-((1R,2S)-2-{[(3aR,4S,9bR)-4-propyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)-1H-benzimidazole-5-carboxamide

HRID 735772Notes

Reaction equation

HRID 735772 reaction equation
Cl.[CH2:2]([C@@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1)[CH2:3][CH3:4].[CH3:27][C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37](O)=[O:38])=[CH:36][C:30]=2[N:29]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O>CN(C=O)C.O>[CH3:27][C:28]1[NH:32][C:31]2[CH:33]=[CH:34][C:35]([C:37]([NH:26][C@@H:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]3[C:18]([N:17]3[C@@H:13]4[C@@H:14]([C@H:5]([CH2:2][CH2:3][CH3:4])[NH:6][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=54)[CH2:15][CH2:16]3)=[O:19])=[O:38])=[CH:36][C:30]=2[N:29]=1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidHCID 67150467(1R,2S)-2-{[(3aR,4R,9bR)-4-(propyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride

Product 1

HCID 1784481662-Methyl-N-((1R,2S)-2-{[(3aR,4S,9bR)-4-propyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)-1H-benzimidazole-5-carboxamideYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of (1R,2S)-2-{[(3aR,4R,9bR)-4-(propyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (203 mg, 0.490 mmol) in DMF (4 ml) were added 2-methyl-1H-benzimidazole-5-carboxylic acid (86.2 mg, 0.490 mmol), triethylamine (0.206 ml, 1.47 mmol) and DEPC (0.0812 ml, 0.490 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 hrs. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with ethyl acetate-methanol (1:0-9:1) to give the title compound (115 mg, 47%) as an amorphous form.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate-methanol (1:0-9:1)

Sources & evidence

ORD record
ord-b77c1f6ef9c040829c13c90cf2f98e73
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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