Methyl N-aminocarbamate Hydrochloride → methyl N-[(E)-[2-(4-methyl-2-pyridin-3-yl-1,3-thiazol-5-yl)-6,7-dihydro-5H-quinolin-8-ylidene]amino]carbamate

HRID 2279267Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][C:10](=O)[C:9]=2[N:8]=1.Cl.[NH2:25][NH:26][C:27](=[O:30])[O:28][CH3:29]>C(O)(=O)C.CO.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11]/[C:10](=[N:25]\[NH:26][C:27](=[O:30])[O:28][CH3:29])/[C:9]=2[N:8]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one (0.030 g, 0.093 mmol), methyl N-aminocarbamate hydrochloride (0.018 g, 014 mmol)) and acetic acid (1drop) were dissolved in methanol (0.9 mL) at ambient temperature and the resulting orange solution was stirred at 75° C. for 1 hour: LC-MS after this time showed reaction completion. The mixture was diluted with ethyl acetate, and then washed successively with saturated aqueous NaHCO3 and then water. The organic phase was, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with 0%-10% Methanol: Dichlormethane gradient gave the title product (29 mg, 79%) as yellow-orange solid. mp: 194-200° C.

Workup

customreaction completion
washwashed successively with saturated aqueous NaHCO3
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography
washeluting with 0%-10% Methanol

Sources & evidence

ORD record: ord-63fb762e457d48a8969450efcf8e9ca2
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133218B2

Reaction notes

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