Sodium Bicarbonate → HCID 178483848, compound

HRID 491795Notes

Reaction equation

HRID 491795 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)=[O:22])=[O:10])[CH2:5][CH2:4]1.[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][CH:41]=O)=[O:37])([CH3:34])([CH3:33])[CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][N:2]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)=[O:22])=[O:10])[CH2:7][CH2:8]1)[CH3:1])=[O:37])([CH3:32])([CH3:33])[CH3:34]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 178484809HCID 178484809, compound

Product 1

HCID 178483848HCID 178483848, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Trans-3-[4-(methylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (250 mg) obtained in Example 221 is suspended in dichloromethane (8 ml), and thereto are added 3-t-butoxycarbonylaminopropanal (198 mg) and triethylamine (160 μl) under ice-cooling, and the mixture is stirred for several minutes. Then, sodium triacetoxy borohydride (243 mg) and the reaction solution is warmed to room temperature, and stirred for 4 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution under ice-cooling, and the mixture is extracted with chloroform. The organic layer is washed successively with water and a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1, then 1/1) to give the title compound (312 mg).

Workup

  1. temperaturecooling
  2. stirringstirred for 4 hours
  3. temperaturecooling
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed successively with water
  6. dry with materiala saturated brine, dried over sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-9336742724454002a0e23657ed0b8223
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

Loading…