Trifluoroacetic acid → 1-(3-Amino-4,6-difluorophenyl)-7-(3-aminoethylazetidin-1-yl)-8-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid trifluoroacetic acid salt

HRID 1415968Notes

Reaction equation

HRID 1415968 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17](F)[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8].C(OC([NH:34][CH2:35][CH2:36][CH:37]1[CH2:40][NH:39][CH2:38]1)=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].Cl.O1CCOCC1>C(N(CC)CC)C>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17]([N:39]4[CH2:40][CH:37]([CH2:36][CH2:35][NH2:34])[CH2:38]4)[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 204431481,4-Dioxane hydrochlorideHCID 378184313-(N-Boc)-(2-aminoethyl)azetidine

Product 1

HCID 867541041-(3-Amino-4,6-difluorophenyl)-7-(3-aminoethylazetidin-1-yl)-8-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Reaction was carried out as in Example 231 except that 1-(3-amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 3-t-butoxycarbonylaminoethylazetidine, and triethylamine were used. For deprotection, trifluoroacetic acid was used rather than 4N hydrochloric acid/dioxane to give the title compound.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-bfff1cb4396e41b8b05fc19877645325
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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