Triethylamine → 8-amino-9-fluoro-3-methyl-10-[(3-cyclopropylaminomethyl)-1-pyrrolidinyl]-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid

HRID 620890Notes

Reaction equation

[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]([C:17]([OH:19])=[O:18])=[CH:12][N:7]3[CH:8]([CH3:11])[CH2:9][O:10][C:5]([C:6]=23)=[C:4](F)[C:3]=1[F:21].[CH:22]1([NH:25][CH2:26][CH:27]2[CH2:31][CH2:30]NC2)[CH2:24][CH2:23]1.[CH2:32]([N:34](CC)CC)C>CN(C)C=O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]([C:17]([OH:19])=[O:18])=[CH:12][N:7]3[CH:8]([CH3:11])[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([N:34]2[CH2:32][CH2:30][CH2:31][CH:27]2[CH2:26][NH:25][CH:22]2[CH2:23][CH2:24]2)[C:3]=1[F:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.96 g (10 mmole) of 8-amino-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][1,4]benzoxazine-6-carboxylic acid, 2.1 g (15 mmole) of N-cyclopropyl-3-pyrrolidinemethanamine, 3.03 g (30 mmole) of triethylamine and 100 ml of N,N-dimethylformamide as heated at 100° C. for four hours. The solvent is removed in vacuo and the residue triturated with water. The aqueous suspension is adjusted to pH 7.2 with 1.0 M hydrochloric acid. The solid is removed by filtration, washed with water, and dried in vacuo to give 8-amino-9-fluoro-3-methyl-10-[(3-cyclopropylaminomethyl)-1-pyrrolidinyl]-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.

Workup

customThe solvent is removed in vacuo
customthe residue triturated with water
customThe solid is removed by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-02192b84240d44c98f15a873eaa47b49
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822801

Reaction notes

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