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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 2372090
Notes
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Reaction equation

HRID 2372090 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13491801N-(Pyrrolidin-3-ylmethyl)cyclopropanamineHCID 143913498-amino-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][1,4]benzoxazine-6-carboxylic acid

Product 1

HCID 679063138-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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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 is 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 1.0M 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

  1. customThe solvent is removed in vacuo
  2. customthe residue triturated with water
  3. customThe solid is removed by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4880d2e8243b403fb57d6c592c02a6f9
Source dataset
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05097032

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes