4-Nitrobenzoic Acid → HCID 86701961, compound

HRID 715787Notes

Reaction equation

N1CC([C:5]2[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=2[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[CH:17]=[CH:18][N:19]=[C:13]3[CH:12]=2)=[O:8])C1.C[CH:25](C)[CH2:26][CH2:27][NH2:28].[CH3:30][CH:31]([CH3:35])[C:32](O)=[O:33].[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>>[N:19]1[CH:18]=[CH:17][N:14]2[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]3[CH:5]=[CH:23][C:22]([CH:26]4[CH2:27][N:28]([C:32](=[O:33])[CH:31]([CH3:35])[CH3:30])[CH2:25]4)=[CH:21][CH:20]=3)=[CH:12][C:13]=12

Participants

Reactant 4

HCID 61084-Nitrobenzoic Acid

HCID 6590Isobutyric Acid

HCID 7894Isoamylamine

HCID 86701962HCID 86701962, compound

Product 1

HCID 86701961HCID 86701961, compound

Procedure

The title compound was prepared as described in Example 1A, substituting -(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-methylpropanoic acid for 4-nitrobenzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.10 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.91 (m, 3H), 7.52 (d, J=1.0 Hz, 1H), 7.48 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.58 (t, J=8.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (t, J=9.0 Hz, 1H), 4.18 (dd, J=8.4, 6.0 Hz, 1H), 3.92 (m, 1H), 3.84 (m, 1H), 3.17 (d, J=5.0 Hz, 1H), 1.00 (dd, J=6.8, 1.6 Hz, 6H); MS (ESI(+)) m/e 377 (M+H)+.

Sources & evidence

ORD record: ord-5af8e905ba1945bab3713181c2d0652c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187472B2

Reaction notes

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