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

HRID 1009948Notes

Reaction equation

HRID 1009948 reaction equation
Cl.[CH3:2][O:3][CH2:4][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.C(N(CC)CC)C.[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1.CCOC(OC(OCC)=O)=O>O1CCCC1.O>[NH:34]1[CH:38]=[CH:37][N:36]=[C:35]1[C:39]1[CH:40]=[CH:41][C:42]([C:43]([NH:26][C@@H:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]2[C:18]([N:17]2[C@@H:13]3[C@@H:14]([C@H:5]([CH2:4][O:3][CH3:2])[NH:6][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=43)[CH2:15][CH2:16]2)=[O:19])=[O:44])=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 14759014-(1H-imidazol-2-yl)benzoic AcidHCID 67150575(1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride

Product 1

HCID 578470834-(1H-Imidazol-2-yl)-N-((1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)benzamideYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in tetrahydrofuran (5 ml) were added triethylamine (0.199 ml, 1.44 mmol), 4-(1H-imidazol-2-yl)benzoic acid (99.0 mg, 0.529 mmol) and DEPC (0.079 ml, 0.529 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was 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 (1:0-4:1) to give the title compound (150 mg, 61%) as an amorphous form.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate-methanol (1:0-4:1)

Sources & evidence

ORD record
ord-0988e3665b3f41649e3e24ce3c86da41
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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