Dimethylformamide → 7-[4-(t-Butyloxycarbonyl aminomethyl)-2-isoindolinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1494810Notes

Reaction equation

HRID 1494810 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:21]([O:25][C:26](NCC1C=CC=C2C=1CNC2)=[O:27])([CH3:24])([CH3:23])[CH3:22].[CH2:39]1[CH2:49][CH2:48][N:47]2C(=N[CH2:44][CH2:45][CH2:46]2)[CH2:41][CH2:40]1.[CH3:50][N:51](C=O)C>>[C:21]([O:25][C:26]([CH:50]([NH2:51])[C:39]1[CH:40]=[CH:41][CH:44]=[C:45]2[C:49]=1[CH2:48][N:47]([C:11]1[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=1[F:16])[CH2:46]2)=[O:27])([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 198284894-(t-Butyloxycarbonylaminomethyl)isoindoline

Product 1

HCID 198284927-[4-(t-Butyloxycarbonyl aminomethyl)-2-isoindolinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Procedure

283 mg of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 300 mg of 4-(t-butyloxycarbonylaminomethyl)isoindoline, 300 mg of DBU, and 2 ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 300 mg of 7-[4-(t-butyloxycarbonyl aminomethyl)-2-isoindolinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Sources & evidence

ORD record
ord-731433415392412b894989874a27e53f
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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