Triethyl methanetricarboxylate → 2-hydroxy-4-oxo-7-(5-trifluoromethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carboxylic acid ethyl ester

HRID 68937

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][C:12]3[N:15]=[C:16]([NH2:18])[S:17][C:11]=3[CH2:10]2)=[N:7][CH:8]=1.[CH:21]([C:32](OCC)=[O:33])([C:27](OCC)=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C(C)=CC=CC=1>[CH2:25]([O:24][C:22]([C:21]1[C:27](=[O:28])[N:15]2[C:16]([S:17][C:11]3[CH2:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][N:7]=4)[CH2:14][CH2:13][C:12]=32)=[N:18][C:32]=1[OH:33])=[O:23])[CH3:26]

Participants

Conditions

Temperature: 145 °C

Procedure

The mixture of 5-(5-trifluoromethyl-pyridin-2-yl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine (5.7 gm, 0.019 mol) and triethyl methantricarboxylate (16.1 ml, 0.076 mol) in xylene (100 ml) was heated at 140-150° C. for 6 hours. Xylene was evaporated and diethyl ether was then added and the suspension was stirred for 15 minutes. It was filtered and washed with ether. The crude solid was digested with dichloromethane (200 ml) and filtered to remove insoluble residue. Dichloromethane layer was distilled off under vacuum to give 1.3 gm of title compound.

Workup

customXylene was evaporated
additiondiethyl ether was then added
filtrationIt was filtered
washwashed with ether
filtrationfiltered
customto remove insoluble residue
distillationDichloromethane layer was distilled off under vacuum

Sources & evidence

ORD record: ord-6e1bf009e1fe450b9247887b89e521b1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822484B2

Linked notes

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