4-Amino-4'-chlorodiphenyl → Ethyl 3-(5-(5-chloro-2-((4'-chloro-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate

HRID 405134

Reaction equation

CN(C(ON1N=N[C:11]2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([CH2:28][CH2:29][NH:30][C:31]([C:33]1[N:38]=[CH:37][C:36]([C:39]2[CH:47]=[C:46]([Cl:48])[CH:45]=[CH:44][C:40]=2[C:41]([OH:43])=O)=[CH:35][CH:34]=1)=[O:32])([OH:27])=[O:26].CCN(C(C)C)C(C)C.[Cl:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]2[CH:70]=[CH:69][C:68]([NH2:71])=[CH:67][CH:66]=2)=[CH:61][CH:60]=1>CCOC(C)=O.CN(C=O)C>[Cl:48][C:46]1[CH:45]=[CH:44][C:40]([C:41](=[O:43])[NH:71][C:68]2[CH:69]=[CH:70][C:65]([C:62]3[CH:61]=[CH:60][C:59]([Cl:58])=[CH:64][CH:63]=3)=[CH:66][CH:67]=2)=[C:39]([C:36]2[CH:35]=[CH:34][C:33]([C:31]([NH:30][CH2:29][CH2:28][C:25]([O:27][CH2:10][CH3:11])=[O:26])=[O:32])=[N:38][CH:37]=2)[CH:47]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Solid HATU (101 mg, 0.27 mmol) was added to a DMF solution (2 mL) of 2-(6-((2-carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid (100 mg, 0.27 mmol), i-Pr2NEt (0.2 mL, 1.1 mmol), and 4′-chloro-[1,1′-biphenyl]-4-amine (57 mg, 0.28 mmol) and the resulting mixture was warmed to 45° C. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

washwashed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-9fe7b119e178466f95b980ab066eb113
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Linked notes

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