Diisopropylethylamine → N-(4-Chloro-3-(N-cyclopropylsulfamoyl)benzyl)-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide

HRID 1845208Notes

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.[NH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([Cl:39])=[C:30]([S:32]([NH:35][CH:36]2[CH2:38][CH2:37]2)(=[O:34])=[O:33])[CH:31]=1.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:39][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:21]([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=2)=[O:22])=[CH:31][C:30]=1[S:32](=[O:34])(=[O:33])[NH:35][CH:36]1[CH2:37][CH2:38]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (60 mg, 0.19 mmol) in N,N-dimethylformamide (1.0 mL) were added 5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide (80 mg, 0.31 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (150 mg, 0.39 mmol) and N,N-diisopropylethylamine (150 μL, 0.86 mmol). The reaction mixture was stirred for 16 hours at 50° C. The reaction mixture was purified by preparative HPLC to afford a light colour solid.

Workup

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

Sources & evidence

ORD record: ord-8a85e301894b44ecab3d3af359c2691d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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