4-Nitrobenzoic Acid → HCID 86702003, compound

HRID 715817Notes

Reaction equation

HRID 715817 reaction equation
[CH2:1]([CH:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)[CH:2]([CH3:4])[CH3:3].CC(C)CCN.[N:16]1[CH:17]=[CH:18][N:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]([C:29]3[S:33][C:32]([C:34]([O-])=[O:35])=[CH:31][CH:30]=3)=[O:28])=[CH:21][C:20]=12.[Li+].[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>>[N:16]1[CH:17]=[CH:18][N:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]([C:29]3[S:33][C:32]([C:34]([N:6]4[CH2:7][CH2:8][CH2:9][CH:5]4[CH2:1][CH:2]([CH3:4])[CH3:3])=[O:35])=[CH:31][CH:30]=3)=[O:28])=[CH:21][C:20]=12

Participants

5

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 3613277124602-03-5HCID 86702001HCID 86702001, compound

Product 1

HCID 86702003HCID 86702003, compound

Procedure

The title compound was prepared as described in Example 1A, substituting), 2-isobutylpyrrolidine for 3-methylbutan-1-amine and lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for 4-nitrobenzoic acid. 1H NMR (300 MHz, DMSO-d6). δ ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=4.0 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.39 (m, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.35-4.23 (m, 1H), 3.78-3.65 (m, 2H), 3.26 (s, 3H), 2.02-1.81 (m, 4H); MS (ESI(+)) m/e 411 (M+H)+.

Sources & evidence

ORD record
ord-b51bf7b789034123b3089b3184112221
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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