Cyclopropylamine → [1,1'-Biphenyl]-3,4'-dicarboxaMide, N3-cyclopropyl-N4'-(cyclopropylMethyl)-6-Methyl-

HRID 1272703Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21](O)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[O:7])[CH2:3][CH2:2]1.[CH:24]1([NH2:27])[CH2:26][CH2:25]1>>[CH:24]1([NH:27][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:6]([NH:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)=[O:7])=[CH:13][CH:12]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 18457809HCID 18457809, compound

Product 1

HCID 24856363[1,1'-Biphenyl]-3,4'-dicarboxaMide, N3-cyclopropyl-N4'-(cyclopropylMethyl)-6-Methyl-

Procedure

N3-Cyclopropyl-N4′-cyclopropylmethyl-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide was synthesised from {4′-[(cyclopropylmethylamino)carbonyl]-6-methyl-1,1′-biphenyl-3-yl}carboxylic acid and cyclopropylamine using method A. NMR: δH [2H6]-DMSO 8.62, (1H, t), 8.43, (1H, d), 7.93, (2H, d), 7.74, (1H, dd), 7.68, (1H, d), 7.46, (2H, d), 7.38, (1H, d), 3.16, (2H, t), 2.83, (1H, m), 2.26, (3H, s), 1.04, (1H, m), 0.67, (2H, m), 0.54, (2H, m), 0.43, (2H, m), 0.24, (2H, m). LCMS: retention time 2.89 min, MH+349.

Sources & evidence

ORD record: ord-41f8e73f128744ec81861fc6f62f98a2
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208629B2

Reaction notes

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