Dimethylformamide → HCID 178461651, compound

HRID 1691694Notes

Reaction equation

HRID 1691694 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]([CH2:22][N:23]([C@@H:31]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)[CH3:32])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:11]2)=[C:5]([F:43])[CH:4]=1)#[N:2].[N-:44]=[N+:45]=[N-:46].[Na+].Cl.C(N(CC)CC)C.CN(C=O)C>O>[F:9][C:7]1[CH:8]=[C:3]([C:1]2[NH:46][N:45]=[N:44][N:2]=2)[CH:4]=[C:5]([F:43])[C:6]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]([CH2:22][N:23]([C@@H:31]([C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[CH3:32])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 66905675tert-butyl {[1-(4-cyano-2,6-difluorophenyl)-4-phenylpiperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate

Product 1

HCID 178461651HCID 178461651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 185 mg of tert-butyl {[1-(4-cyano-2,6-difluorophenyl)-4-phenylpiperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate, 414 mg of sodium azide, 876 mg of triethylamine hydrochloride, and 4.0 mL of DMF was stirred at 120° C. overnight. The reaction mixture was cooled to room temperature, and water added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain tert-butyl ({1-[2,6-difluoro-4-(1H-tetrazol-5-yl)phenyl]-4-phenylpiperidin-3-yl}methyl)[(1R)-1-(1-naphthyl)ethyl]carbamate as a crude product (beige foamy substance, 208 mg). ESI+: 625

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a72dc270815e4cd181eea7a69f81a27f
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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