4-Nitrobenzoic Acid → HCID 72194965, compound

HRID 717910Notes

Reaction equation

HRID 717910 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]([NH:16][C:17](=[O:28])[NH:18][C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)[CH:13]=[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]=[C:14]([NH:16][C:17]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([NH:5][CH2:4][CH2:3][C:2]4[CH:6]=[CH:40][CH:32]=[CH:33][CH:1]=4)=[O:25])=[CH:26][CH:27]=3)=[O:28])[CH:13]=[CH:12][C:11]=12

Participants

4

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 86701923HCID 86701923, compound

Product 1

HCID 72194965HCID 72194965, compound

Procedure

The title compound was prepared as described in Example 1A, substituting 2-phenylethanamine for 3-methylbutan-1-amine and 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6/D2O, Temp=90° C.) δ ppm 9.33 (dd, J=1.9, 0.8 Hz, 1H), 8.32 (d, J=1.8 Hz, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.90 (d, J=9.7 Hz, 1H), 7.85-7.74 (m, 3H), 7.61-7.51 (m, 2H), 7.35-7.20 (m, 5H), 3.49 (dd, J=8.1, 6.9 Hz, 2H), 2.94-2.79 (m, 2H); MS (ESI(+)) m/e 400 (M+H)+.

Sources & evidence

ORD record
ord-79c80744e1f0489482d95dae06de4b8a
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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