Sodium hydride → HCID 15021553, compound

HRID 465381Notes

Reaction equation

HRID 465381 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](Cl)[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1.[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH:36]([OH:39])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C1CCN2C(=NCCC2)CC1.[H-].[Na+]>CN(C=O)C>[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH:36]([O:39][C:16]2[N:17]=[C:18]3[C:13]([C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10][N:9]3[C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:14][C:15]=2[F:20])[CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1268243Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 15021553HCID 15021553, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 325 mg of ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, 325 mg of 1-t-butoxycarbonyl-3hydroxypyrrolidine, 194 mg of DBU and 3 ml of DMF was added 46 mg of 55% sodium hydride while the former was stirred at room temperature. After the resultant mixture was stirred for 1.5 hours at room temperature, the reaction mixture was treated in a similar manner to Example 1-(1), whereby 240 mg of ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate was obtained.

Sources & evidence

ORD record
ord-e7b98fc1630c4088b316933dd4d74bfc
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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