HCID 178456121, compound → HCID 178434922, compound

HRID 1982613Notes

Reaction equation

Cl[CH:2]([C:4]1[C:13]([C:14]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)=[O:15])=[C:12]([OH:22])[C:11]2[C:6](=[C:7]([C:23]([F:26])([F:25])[F:24])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3]>C(O)(=O)C>[CH3:3][CH:2]1[C:4]2=[N:5][C:6]3[C:7]([C:23]([F:26])([F:25])[F:24])=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]([OH:22])=[C:13]2[C:14](=[N:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[O:15]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6 g of 2-(1-chloroethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide [described in Examples 5 and 14 of U.S. patent application Ser. No. 262,952]and 50 ml of acetic acid was placed in an oil bath heated to 140° C. and held there for 9 minutes and then cooled to room temperature. The mixture was held at 16° C. for one hour and was vacuum filtered. The product was washed with acetic acid, then with ether and dried under reduced pressure at 80° C. to obtain 5.4 g of 1,3-dihydro-3-methyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo[3,4-b]quinoline-9-ol in the form of an acetate. The latter was added to 100 water to which was added an aqueous saturated sodium bicarbonate solution to adjust the pH to 6. The mixture was vacuum filtered and the product was washed with water and dried under reduced pressure at 70° C. to obtain 4.2 g of 1,3-dihydro-3-methyl-1-[(2-thiazolyl)-imino]-5-trifluoromethyl-furo [3,4-b]quinoline-9-ol melting at 260° C. (decomposition).

Workup

temperaturecooled to room temperature
waitThe mixture was held at 16° C. for one hour
filtrationfiltered
washThe product was washed with acetic acid
dry with materialwith ether and dried under reduced pressure at 80° C.

Sources & evidence

ORD record: ord-aa64d6b49af54c789437fbe39a2c003d
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04596875

Reaction notes

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