1,2-Dichloroethane → HCID 67519695, compound

HRID 12760Notes

Reaction equation

HRID 12760 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:18])[NH:9][C:10](=[O:17])[N:11]([CH2:13][CH2:14][CH:15]=O)[CH:12]=1.[F:19][C:20]([F:34])([F:33])[C:21]1[CH:26]=[CH:25][C:24]([C@:27]23[CH2:32][C@H:31]2[CH2:30][NH:29][CH2:28]3)=[CH:23][CH:22]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:53]CCCl>C(OCC)C>[ClH:53].[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:18])[NH:9][C:10](=[O:17])[N:11]([CH2:13][CH2:14][CH2:15][N:29]2[CH2:30][C@H:31]3[C@:27]([C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:34])[F:33])=[CH:26][CH:25]=4)([CH2:32]3)[CH2:28]2)[CH:12]=1

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 58994234HCID 58994234, compoundHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 67519695HCID 67519695, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-[5-(3-methyl-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde (Prep29, 16 mg, 0.04 mmol) in DCE (3 mL), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 20 mg, 0.05 mmol) in DCE (1 mL), AcOH (6 μl, 0.05 mmol) and NaBH(AcO)3 (30 mg, 0.08 mmol) were added and the mixture was stirred at room temperature overnight. Diethylether was then added and the mixture was washed with 1N solution of HCl, then with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1) to give the title compound (8 mg, 42% yield) as a free base.

Workup

  1. washthe mixture was washed with 1N solution of HCl
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1)

Sources & evidence

ORD record
ord-71bc8e05cb2d486db2d4ec7e9086ab86
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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