Acetic Acid → HCID 67519703, compound

HRID 12762Notes

Reaction equation

HRID 12762 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:19])[NH:9][C:10](=[O:18])[N:11]([CH2:13][CH2:14][CH2:15][CH:16]=O)[CH:12]=1.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([C@:28]23[CH2:33][C@H:32]2[CH2:31][NH:30][CH2:29]3)=[CH:24][CH:23]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+].[Cl:56]C(Cl)C>>[ClH:56].[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:19])[NH:9][C:10](=[O:18])[N:11]([CH2:13][CH2:14][CH2:15][CH2:16][N:30]2[CH2:31][C@H:32]3[C@:28]([C:25]4[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:35])[F:34])=[CH:27][CH:26]=4)([CH2:33]3)[CH2:29]2)[CH:12]=1

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58994229HCID 58994229, compoundHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 67519703HCID 67519703, compoundYield 48%

Procedure

To a solution of 4-[5-(3-methyl-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-butyraldehyde (Prep32, 30 mg, 0.11 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 21 mg, 0.09 mmol), AcOH (6 μl, 0.1 mmol) in dichloroethane (1.5 mL) and NaBH(AcO)3 (24 mg, 0.11 mmol) were added at 0° C. The reaction was stirred for 30 minutes at room temperature then 2N NaOH (1 mL) was added and the product extracted with ethyl acetate. The organic phase washed with brine, dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5) to give the title compound (26 mg, 48% yield) as a free base.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washThe organic phase washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5)

Sources & evidence

ORD record
ord-6bcccc6421c74c5a941f7f2f2129b8e2
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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