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Diisopropylethylamine → N-(1-(4-Chloro-3-(methylsulfonyl)phenyl)ethyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

HRID 1845191
Notes
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Reaction equation

HRID 1845191 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.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH2:33])[CH3:32])=[CH:27][C:26]=1[S:34]([CH3:37])(=[O:36])=[O:35].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:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH:33][C:21]([C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[CH:13]=[C:12]([C:14]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:15])[CH:11]=2)=[O:23])[CH3:32])=[CH:27][C:26]=1[S:34]([CH3:37])(=[O:35])=[O:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 581881711-(4-Chloro-3-(methylsulfonyl)phenyl)ethanamine

Product 1

HCID 58188146
N-(1-(4-Chloro-3-(methylsulfonyl)phenyl)ethyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °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 1-(4-chloro-3-(methylsulfonyl)phenyl)ethanamine (50 mg, 0.21 mmol), 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 50° C. LC-MS indicated the reaction was complete. The mixture was purified by preparative HPLC to afford the final product as an off white solid.

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-945804d4ae6e4c1cae5b88fc16a22511
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946439B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes