octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide → octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide

HRID 243626Notes

Reaction equation

HRID 243626 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.COC(=O)CCCCCCC(NC1SC=C(C2C=CC=C(N)C=2)N=1)=O>>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 16733292octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amideHCID 44550930octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

Product 1

HCID 53323224octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide

Procedure

Compound 21 was prepared using the methodology described for the preparation of compound 18, by substituting compound 14 with compound 20. Yield (0.276 g, 79.8%). 1H NMR (300 MHz, CDCl3) δ 7.21 (1H, t, J=7.7 Hz), 7.07 (1H, d, J=8.2 Hz), 6.99 (2H, s), 6.69 (1H, d, J=7.8 Hz), 2.49 (2H, t, J=7.3 Hz), 2.40 (2H, t, J=7.1 Hz), 1.78 (2H, brs), 1.69 (2H, t, J=6.7 Hz), 1.50-1.35 (4H, m). 13C NMR (75 MHz, CDCl3) δ 179.6, 172.2, 160.8, 149.7, 147.1, 135.0, 130.2, 117.3, 115.6, 113.5, 108.1, 36.7, 34.4, 29.1, 28.9, 25.5, 24.9.

Workup

  1. customYield (0.276 g, 79.8%)

Sources & evidence

ORD record
ord-b424cbf084cb4301a6a576412fef1883
Source dataset
uspto-grants-2014_02
Patent number
US08653278B2

Reaction notes

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