Guanidine Hydrochloride → HCID 13772795, compound

HRID 978521Notes

Reaction equation

HRID 978521 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CN(C)[CH:8]=[CH:9][C:10]([C:12]1[C:21]([F:22])=[C:20]2[C:15]([C:16](=[O:30])[C:17]([C:25]([O:27]CC)=[O:26])=[CH:18][N:19]2[CH2:23][CH3:24])=[CH:14][C:13]=1[F:31])=O>>[NH2:4][C:3]1[N:5]=[C:10]([C:12]2[C:21]([F:22])=[C:20]3[C:15]([C:16](=[O:30])[C:17]([C:25]([OH:27])=[O:26])=[CH:18][N:19]3[CH2:23][CH3:24])=[CH:14][C:13]=2[F:31])[CH:9]=[CH:8][N:2]=1

Participants

3

Reactant 2

HCID 5742Guanidine HydrochlorideHCID 54568569HCID 54568569, compound

Product 1

HCID 13772795HCID 13772795, compound

Procedure

To 1.5 g (4.1 mmol) of the ethyl 7-(2'-dimethylaminoethenyl)carbonyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 35 ml of t-butanol was added at 60° C. a mixture of 2.49 g 2.5 equivalents) of 2-N-(benzyloxycarbonyl)aminoacetamidine hydrochloride, and 1.15 g (2.5 eq) of potassium t-butoxide in 50 ml of t-butanol. After four hours, 452 mg more of potassium t-butoxide was added. The mixture was stirred overnight at 60° C. It was poured into dilute hydrochloric acid and extracted with dichloromethane. The dichloromethane was concentrated and the residue was purified by column chromatography to give 530 mg of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[2-[[(phenylmethoxy)carbonyl]aminomethy]-4-pyrimidinyl]-3-quinolinecarboxylic acid as a yellow solid, mp 195°-196° C. This material was then treated with hydrobromic acid in acetic acid, for three hours. The mixture was poured into ethylacetate:diethyl ether. The solids were filtered and then dissolved in aqueous ammonia pH 10.8° C. This mixture was concentrated to one-fourth volume and the solids filtered to give 173 mg of 7-[2-(aminomethyl)-4-pyrimidinyl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 285°-289° C. In a similar fashion the 7-(2-amino-4-pyrimidinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 285°-286° C. (42a) was prepared using guanidine hydrochloride and ethyl 7-(2'-dimethylaminoethenyl)carbonyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate.

Sources & evidence

ORD record
ord-c2364d03ab94405e85c770b588565fed
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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