Triethylamine → 7-(4-Amino-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1494818Notes

Reaction equation

HRID 1494818 reaction equation
[NH2:1][CH2:2][C:3]1C=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]1[C:13]([F:30])=[CH:14][C:15]3[C:25](=[O:26])[C:24]([C:27]([OH:29])=[O:28])=[CH:23][N:17]4[CH:18]([CH3:22])[CH2:19]OC=1[C:16]=34)[CH2:6]2.C(OC(C1C(=O)C2C(=NC(Cl)=C(F)C=2)[N:38](C2CC2)C=1)=O)C.NC1C=CC=C2C=1CNC2.C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:3]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([C:12]1[N:38]=[C:16]3[C:15]([C:25](=[O:26])[C:24]([C:27]([OH:29])=[O:28])=[CH:23][N:17]3[CH:18]3[CH2:22][CH2:19]3)=[CH:14][C:13]=1[F:30])[CH2:8]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 14795861Isoindolin-4-amineHCID 5424461510-(5-aminomethyl-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido [1,2,3-de][1,4]-benzoxazine-6-carboxylic acid

Product 1

HCID 147958747-(4-Amino-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

310 mg of 1 cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 270 mg of 4-aminoisoindoline, 0.42 ml of triethylamine, and 5 ml of anhydrous chloroform were processed in a similar manner as in Example 107 to produce 88 mg of 7-(4-amino-2- isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8- naphthyridine-3-carboxylic acid.

Sources & evidence

ORD record
ord-52b70de95dd946e7af42d2aaf838f1d7
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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