4-Nitrobenzoic Acid → HCID 72699526, compound

HRID 717934Notes

Reaction equation

HRID 717934 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]=[C:14]([CH2:16][NH:17][C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)=[O:19])[CH:13]=[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]=[C:14]([CH2:16][NH:17][C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])=[O:25])=[CH:22][CH:21]=3)=[O:19])[CH:13]=[CH:12][C:11]=12

Participants

4

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 86701948HCID 86701948, compound

Product 1

HCID 72699526HCID 72699526, compound

Procedure

The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.15 (t, J=5.8 Hz, 1H), 8.55-8.47 (m, 2H), 8.00-7.84 (m, 5H), 7.54 (dd, J=5.1, 4.1 Hz, 2H), 7.23 (dd, J=9.3, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 3.30-3.21 (m, 2H), 1.62 (dp, J=13.3, 6.6 Hz, 1H), 1.49-1.37 (m, 2H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 365 (M+H)+.

Sources & evidence

ORD record
ord-5d3e9b503faa4502a498facbbe668cce
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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