Dimethylformamide → HCID 86761012, compound

HRID 1437679Notes

Reaction equation

HRID 1437679 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([NH:37][CH2:38][C:39](O)=[O:40])(OC(C)(C)C)=[O:31].CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.CN([CH:64]=[O:65])C>O>[F:2][C:3]([F:29])([F:28])[C:64]([OH:65])=[O:31].[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:39](=[O:40])[CH2:38][NH2:37])[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86761012HCID 86761012, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of the compound (35 mg) obtained in Example 1, Boc-glycine (15 mg) and Et3N (22 μl) in DMF (2.0 ml), WSC.HCl (17 mg) and HoBt.H2O (13 mg) were added, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, and dried, and the solvent was evaporated under reduced pressure, and then the residue was purified by preparative HPLC. To the obtained product, trifluoroacetic acid (1 ml) was added and the reaction mixture was stirred for 1 hour, and then the solvent was evaporated to obtain the title compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC
  6. additionTo the obtained product, trifluoroacetic acid (1 ml) was added
  7. stirringthe reaction mixture was stirred for 1 hour
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-95fbe56526c748f0a45524356586ebfd
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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