Diisopropylethylamine → (R)-N-(1-(5-Chloro-1-methyl-1H-pyrazol-4-yl)ethyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

HRID 1845217Notes

Reaction equation

HRID 1845217 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21](O)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[Cl:25][C:26]1[N:30]([CH3:31])[N:29]=[CH:28][C:27]=1[C@H:32]([NH2:34])[CH3:33].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>[Cl:25][C:26]1[N:30]([CH3:31])[N:29]=[CH:28][C:27]=1[C@H:32]([NH:34][C:21]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:13]=[C:12]([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:11]=1)=[O:22])[CH3:33]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581879754'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acidHCID 67053768(R)-1-(5-chloro-1-methyl-1H-pyrazol-4-yl)ethanamine hydrochloride

Product 1

HCID 58188192(R)-N-(1-(5-Chloro-1-methyl-1H-pyrazol-4-yl)ethyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 20 mL vial was charged with 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (30 mg, 0.097 mmol), (R)-1-(5-chloro-1-methyl-1H-pyrazol-4-yl)ethanamine hydrochloride (24 mg, 0.12 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (92 mg, 0.24 mmol), N,N-diisopropylethylamine (0.068 mL, 0.39 mmol), and N,N-dimethylformamide (1.0 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was purified by preparative HPLC to get the product as a light yellow solid.

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-579e9de99dac489aaf7496bd96003e9d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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