Water → HCID 57847233, compound

HRID 1009936Notes

Reaction equation

HRID 1009936 reaction equation
Cl.[CH3:2][C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C@H:8]1[C@H:17]2[CH2:18][CH2:19][N:20]([C:21]([C@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[NH2:29])=[O:22])[C@H:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9]1.C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>ClCCl>[CH3:2][C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C@H:8]1[C@H:17]2[CH2:18][CH2:19][N:20]([C:21]([C@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[NH:29][C:37](=[O:44])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:22])[C@H:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67150457HCID 67150457, compound

Product 1

HCID 57847233HCID 57847233, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (1R,2S)-2-{[(3aR,4R,9bR)-4-(2-methyl-3-furyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (201 mg, 0.445 mmol) in dichloromethane (5 ml) were added triethylamine (0.203 ml, 1.47 mmol) and benzoylchloride (0.0568 ml, 0.490 mmol) under ice-cooling. The reaction mixture was stirred overnight at room temperature, water was added, and extracted with dichloromethane. The extract was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1-3:2, v/v) to give the title compound (176 mg, 82%) as an amorphous form.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. washeluted with hexane-ethyl acetate (4:1-3:2

Sources & evidence

ORD record
ord-0ee1ac3b224342e3970b48f27bf1808c
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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