4-Nitrobenzoic Acid → HCID 86701956, compound

HRID 715781Notes

Reaction equation

HRID 715781 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[N:7]1[CH:8]=[CH:9][N:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:28])[NH:19][C:20]3[S:21][C:22]([C:25]([OH:27])=O)=[CH:23][N:24]=3)=[CH:12][C:11]=12.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>>[N:7]1[CH:8]=[CH:9][N:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([NH:19][C:20]3[S:21][C:22]([C:25]([NH:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])=[O:27])=[CH:23][N:24]=3)=[O:28])=[CH:12][C:11]=12

Participants

4

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 86701955HCID 86701955, compound

Product 1

HCID 86701956HCID 86701956, compound

Procedure

The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.49 (d, J=7.8 Hz, 1H), 8.21 (t, J=5.9 Hz, 1H), 7.88-7.89 (m, J=1.4 Hz, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.39 (s, 1H), 7.18 (t, J=5.8 Hz, 1H), 6.83 (dd, J=6.8, 1.7 Hz, 1H), 4.38 (d, J=6.1 Hz, 2H), 3.16-3.25 (m, 2H), 1.52-1.67 (m, 1H), 1.38 (q, J=6.9 Hz, 2H), 0.83-0.91 (m, 7H); MS (ESI(+)) m/e 387 (M+H)+.

Sources & evidence

ORD record
ord-11822c9d3a6941979807bb28cf2d61fb
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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