4-Nitrobenzoic Acid → HCID 86701951, compound

HRID 715778Notes

Reaction equation

HRID 715778 reaction equation
C[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]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=3)=[O:19])=[CH:12][C:11]=12.[N+](C1C=CC([C:36](O)=[O:37])=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]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:5][CH2:4][C@@H:3]4[CH2:2][CH2:6][O:37][CH2:36]4)=[O:26])=[CH:22][CH:21]=3)=[O:19])=[CH:12][C:11]=12

Participants

4

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 86701952HCID 86701952, compound

Product 1

HCID 86701951HCID 86701951, compound

Procedure

The title compound was prepared as described in Example 1A, substituting (5)-(tetrahydrofuran-3-yl)methanamine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.69 (t, J=5.7 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.07-7.71 (m, 5H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.80-3.56 (m, 4H), 3.48 (dd, J=8.5, 5.2 Hz, 1H), 2.02-1.87 (m, 1H), 1.68-1.53 (m, 1H), 1.32-1.00 (m, 2H); MS (ESI(+)) m/e 379 (M+H)+.

Sources & evidence

ORD record
ord-b22c0c68fd8c48739f2db470625a3d08
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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