Ammonia → HCID 57847125, compound

HRID 735776Notes

Reaction equation

HRID 735776 reaction equation
Cl.Cl.C(OC[N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[C@H:16]1[C@H:25]2[CH2:26][CH2:27][N:28]([C:29]([C@H:31]3[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]3[NH2:37])=[O:30])[C@H:24]2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:17]1)(=O)C(C)(C)C.[C:38]([C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)#[N:39].N>C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].CO>[C:38]([C:40]1[CH:48]=[CH:47][C:43]([C:44]([NH:37][C@@H:32]2[CH2:33][CH2:34][CH2:35][CH2:36][C@@H:31]2[C:29]([N:28]2[C@@H:24]3[C@@H:25]([C@H:16]([C:12]4[NH:13][CH:14]=[CH:15][N:11]=4)[NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=43)[CH2:26][CH2:27]2)=[O:30])=[O:45])=[CH:42][CH:41]=1)#[N:39]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 801724-Cyanobenzoyl chlorideHCID 67150587HCID 67150587, compound

Product 1

HCID 57847125HCID 57847125, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

[2-((3aR,4R,9bR)-1-{[(1S,2R)-2-aminocyclohexyl]carbonyl}-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-4-yl)-1H-imidazol-1-yl]methyl pivalate dihydrochloride (7.16 g, 13.0 mmol) was dissolved in ethyl acetate (170 ml) and 10% aqueous sodium carbonate solution (140 ml), and 4-cyanobenzoyl chloride (2.59 g, 15.6 mmol) was added under ice-cooling. The reaction mixture was stirred at room temperature for 2 hrs., and the separated aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (1:0-10:1, v/v) to give an amorphous form. This was dissolved in methanol (200 ml), 28% aqueous ammonia (100 ml) was added dropwise, and the mixture was stirred for 5 hrs. The solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (1:0-5:1, v/v) to give the title compound (6.06 g, 94%) as an amorphous form.

Workup

  1. temperaturecooling
  2. extraction, and the separated aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washeluted with ethyl acetate-methanol (1:0-10:1
  6. customv/v) to give an amorphous form
  7. stirringthe mixture was stirred for 5 hrs
  8. customThe solvent was evaporated under reduced pressure
  9. washeluted with ethyl acetate-methanol (1:0-5:1

Sources & evidence

ORD record
ord-9b985b610d444fb6986bb029f3df8486
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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