4-Nitrobenzoic Acid → HCID 86702012, compound

HRID 715825Notes

Reaction equation

HRID 715825 reaction equation
[CH3:1]C(C)CCN.[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+:29]([C:32]1C=C[C:35]([C:36]([OH:38])=O)=[CH:34][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:21]=[CH:22][C:23]([C:24]([N:29]4[CH2:32][CH2:33][CH2:34][C@@H:35]4[CH2:36][O:38][CH3:1])=[O:25])=[CH:27][CH:28]=3)=[CH:12][C:11]=12

Participants

4

Reactant 3

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

Product 1

HCID 86702012HCID 86702012, compound

Procedure

The title compound was prepared as described in Example 1A, substituting (2R)-2-(methoxymethyl)pyrrolidine 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 9.18 (t, J=4.8 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.95 (d, J=8.3 Hz, 2H), 7.88 (s, 1H), 7.57 (d, J=7.7 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.62-2.88 (br m, 8H), 2.05-1.64 (br m, 4H); MS (ESI(+)) m/e 393 (M+H)+.

Sources & evidence

ORD record
ord-a962260e3221424babb57ff3f63637d6
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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