Dichloromethane → HCID 15603140, compound

HRID 550555Notes

Reaction equation

HRID 550555 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.[CH3:17][N:18]1[C:22]([S:23][CH3:24])=[N:21][N:20]=[C:19]1[CH2:25][CH2:26][CH2:27][CH:28]=O.[BH4-].[Na+].C(Cl)[Cl:33]>ClCCCl.C(O)(=O)C.O>[ClH:33].[CH3:17][N:18]1[C:22]([S:23][CH3:24])=[N:21][N:20]=[C:19]1[CH2:25][CH2:26][CH2:27][CH2:28][N:11]1[CH2:12][C@H:13]2[C@:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=3)([CH2:14]2)[CH2:10]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 57691907HCID 57691907, compound2×HCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 15603140HCID 15603140, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (40 mg) and 4-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]butanal (40 mg) in 1,2-dichloroethane (4 ml) sodium borohydride (76 mg) and acetic acid (20 μl) were added and the reaction mixture was stirred overnight at room temperature. Then an additional amount of 4-[4-methyl-5-(methylthio)-4H-1, 2,4-triazol-3-yl]butanal (48 mg), sodium borohydride (76 mg) and acetic acid (20 μl) were added and the stirring continued for 2 days then DCM and water were added to the reaction mixture. The solvent was removed under reduced pressure affording a crude product that was purified by chromatography to give the free base of the title compound. To a solution of this compound in DCM (1 mL) HCL 1N in diethylehter was added (0.12 mL) and the solvent removed under reduced pressure to give the title compound (67 mg) as a slightly hygroscopic solid.

Workup

  1. waitthe stirring continued for 2 days
  2. customThe solvent was removed under reduced pressure
  3. customaffording a crude product that
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-cc03ba2d723a4cd384b65cb72bb758ce
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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