Diisopropylethylamine → N-(3-Hydroxy-1-(6-(trifluoromethyl)pyridin-3-yl)propyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

HRID 1845209Notes

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]([OH:23])=O)[CH:9]=2)=[CH:4][CH:3]=1.[NH2:24][CH:25]([C:29]1[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=1)[CH2:26][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][CH2:26][CH:25]([NH:24][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[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:15])[CH:11]=1)=[O:23])[C:29]1[CH:30]=[N:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (17 mg, 0.055 mmol) in N,N-dimethylformamide (0.5 mL) were added 3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol (47 mg, 0.21 mmol) (WO 2008/130481), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (80 mg, 0.21 mmol) and N,N-diisopropylethylamine (80 μL, 0.46 mmol). The reaction mixture was stirred for 16 hours at 30° C. The reaction mixture was purified by preparative HPLC to afford a white solid.

Workup

customThe reaction mixture was purified by preparative HPLC
customto afford a white solid

Sources & evidence

ORD record: ord-9b119436cb704afba53756d769f8c305
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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