4-Nitrobenzoic Acid → HCID 86702000, compound

HRID 717975Notes

Reaction equation

HRID 717975 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.CC(C)CCN.[N:15]1[CH:16]=[CH:17][N:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([C:28]3[S:32][C:31]([C:33]([O-])=[O:34])=[CH:30][CH:29]=3)=[O:27])=[CH:20][C:19]=12.[Li+].[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>>[N:15]1[CH:16]=[CH:17][N:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([C:28]3[S:32][C:31]([C:33]([N:5]4[CH2:6][CH2:7][CH2:8][C@@H:4]4[CH2:3][O:2][CH3:1])=[O:34])=[CH:30][CH:29]=3)=[O:27])=[CH:20][C:19]=12

Participants

5

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 86702001HCID 86702001, compound

Product 1

HCID 86702000HCID 86702000, compound

Procedure

The title compound was prepared as described in Example 1A, substituting), (R)-2-(methoxymethyl)pyrrolidine 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) 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 399 (M+H)+.

Sources & evidence

ORD record
ord-ae5ef31b33ad4545be94e17eb8bab8c5
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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