4-Nitrobenzoic Acid → HCID 86702014, compound

HRID 717985Notes

Reaction equation

HRID 717985 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](O)=[O:25])=[CH:22][CH:21]=3)=[O:19])=[CH:12][C:11]=12.[N+]([C:32]1[CH:40]=CC(C(O)=O)=C[CH:33]=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](=[O:19])[C:20]3[CH:28]=[CH:27][C:23]([C:24]([N:5]4[CH2:4][CH2:3][CH2:2][CH:6]4[CH:32]([CH3:40])[CH3:33])=[O:25])=[CH:22][CH:21]=3)=[CH:12][C:11]=12

Participants

4

Reactant 3

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

Product 1

HCID 86702014HCID 86702014, compound

Procedure

The title compound was prepared as described in Example 1A, substituting (propan-2-yl)pyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.44-9.36 (m, 1H), 8.86 (d, J=6.9 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 8.01-7.95 (m, 2H), 7.80 (s, 1H), 7.65-7.59 (m, 2H), 7.49 (d, J=7.6 Hz, 1H), 4.69 (d, J=5.8 Hz, 2H), 4.15-4.05 (m, 1H), 3.47-3.19 (m, 2H), 2.39-2.26 (m, 1H), 1.96-1.57 (m, 4H), 0.93-0.85 (m, 6H); MS (ESI(+)) m/e 391 (M+H)+.

Sources & evidence

ORD record
ord-d208d798866d40f5862b34a1c753515d
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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