Pyridine → Methyl [1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluorophenyl)cyclopropyl]acetate

HRID 1476085Notes

Reaction equation

HRID 1476085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([C:26]2([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:28][CH2:27]2)[CH:22]=[CH:23][C:24]=1[F:25].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.N1C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([NH:18][C:19]2[CH:20]=[C:21]([C:26]3([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:28]3)[CH:22]=[CH:23][C:24]=2[F:25])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58288274Methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetateHCID 58288396(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid

Product 1

HCID 86719143Methyl [1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluorophenyl)cyclopropyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 70 mg (0.31 mmol) of (2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid, 84 mg (0.31 mmol) of methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetate, 179 mg (0.47 mmol) of 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) and 0.6 ml of pyridine in 2.4 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the mixture was separated directly, without further work-up, by preparative HPLC. This gave 106 mg (0.22 mmol, 72% of theory) of the title compound as a colourless oil.

Workup

  1. customthe mixture was separated directly, without further work-up, by preparative HPLC

Sources & evidence

ORD record
ord-d3a7cea8f4fe4158b332a4a740daa771
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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