Hydrochloric Acid → (2s)-2-[(4-Bromophenyl)(4-fluorophenyl)methoxy]-n-(cyanomethyl)-4-methylpentanamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](O)=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:26][CH2:27][C:28]#[N:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([NH:29][CH2:28][C:27]#[N:26])=[O:12])=[CH:6][CH:7]=1Participants
8
Reactant 5
HCID 313Hydrochloric Acid
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 11491918Aminoacetonitrile hydrochloride
HCID 69470167(2S)-2-[(4-Bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoic acidProduct 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2S)-2-[(4-bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoic acid of step 4 (0.35 mmol, 151 mg) in DMF (3 mL) was added aminoacetonitrile hydrochloride (0.38 mmol) and HATU (0.38 mmol, 145 mg). Diisopropylethylamine (0.96 mmol, 123 mg) was added last, the mixture was stirred at r.t. for 3 days. Ether was added, followed by 1 N HCl. The mixture was separated after agitation. The organic extract was washed with 0.1 N HCl, water and brine and dried over anhyd. MgSO4. Concentration of the organic extracts followed by chromatography gave the title amide.
Workup
- customThe mixture was separated after agitation
- extractionThe organic extract
- washwas washed with 0.1 N HCl, water and brine
- customdried over anhyd
Sources & evidence
- ORD record
- ord-af7dc86045854a029820b23907419d2f
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279478B2
Reaction notes
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