Dimethylformamide → 2',3'-Difluoro-5-(5-methyl-pyridin-2-yl)-biphenyl-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

HRID 2278757Notes

Reaction equation

HRID 2278757 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:12]=[C:11]([C:22]([OH:24])=O)[CH:10]=1.[NH2:25][C@@H:26]([CH3:29])[CH2:27][OH:28].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[OH:28][CH2:27][C@@H:26]([NH:25][C:22]([C:11]1[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:12]=1)=[O:24])[CH3:29]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 80307L-AlaninolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584493602',3'-Difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid

Product 1

HCID 451382532',3'-Difluoro-5-(5-methyl-pyridin-2-yl)-biphenyl-3-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide

Procedure

A round bottom flask was charged with 2′,3′-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid (30.00 mg, 0.09222 mmol), (2S)-2-Aminopropan-1-ol (8.3119 mg, 0.11066 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.087662 g, 0.23055 mmol), N,N-diisopropylethylamine (0.064252 mL, 0.36888 mmol), N,N-dimethylformamide (0.157 mL, 2.03 mmol) and the reaction stirred over night at room temperature. The solvent was removed under reduced pressure and the residue purified by prep HPLC to get the compound as white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-9f6ccae33ed14d1995ab7cac63e583ba
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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