Cyclohexylamine → 7-Hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid cyclohexylamide

HRID 902514Notes

Reaction equation

[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:23])[NH:15][C:16]2[C:20]([C:21]=1[OH:22])=[CH:19][S:18][CH:17]=2)=O)C>C1(C)C=CC=CC=1>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:23])[NH:15][C:16]3[C:20]([C:21]=2[OH:22])=[CH:19][S:18][CH:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

Cyclohexylamine (4.6 mL, 40.12 mmol) was added to a solution of 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (39) (3.2 g, 82.70 mmol) in toluene and heated at 130° C. for 4 h. The solution was cooled and excess solvent was distilled off under vacuum. The residue was taken in CH2Cl2, sonicated briefly, and filtered to yield 3.5 g (89%) of 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid cyclohexylamide as white solids. MP 244° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.26-1.41 (m, 5H), 1.53 (m, 1H), 1.65 (m, 2H), 1.86 (m, 2H), 3.81 (m, 1H), 6.95 (s, 1H), 8.25 (s, 1H) ppm; MS m/z=293 amu (M++1).

Workup

temperatureThe solution was cooled
distillationexcess solvent was distilled off under vacuum
customsonicated briefly
filtrationfiltered

Sources & evidence

ORD record: ord-7bfb758316ef43fab1d2998b651c214b
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365200B2

Reaction notes

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