1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86746140, compound

HRID 1885859Notes

Reaction equation

HRID 1885859 reaction equation
Br.Br.C([NH:10][C@@H:11]1[C@@H:16]2[CH2:17][CH2:18][C@@H:13]([CH2:14][NH:15]2)[CH2:12]1)C1C=CC=CC=1.[CH:19]1([N:22]2[C:31]3[C:26](=[CH:27][C:28]([F:33])=[C:29](F)[CH:30]=3)[C:25](=[O:34])[C:24]([C:35]([OH:37])=[O:36])=[CH:23]2)[CH2:21][CH2:20]1.C1CCN2C(=NCCC2)CC1>>[NH2:10][C@@H:11]1[C@@H:16]2[CH2:17][CH2:18][C@@H:13]([CH2:14][N:15]2[C:29]2[CH:30]=[C:31]3[C:26]([C:25](=[O:34])[C:24]([C:35]([OH:37])=[O:36])=[CH:23][N:22]3[CH:19]3[CH2:21][CH2:20]3)=[CH:27][C:28]=2[F:33])[CH2:12]1

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 57473424HCID 57473424, compound

Product 1

HCID 86746140HCID 86746140, compound

Procedure

In a manner similar to that of Example 14, the title compound of Example 12 (0.80 g) was coupled to 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid in the presence of DBU, and the product was similarly subjected to catalytic hydrogenation to remove the benzyl group, yielding 0.24 g of the title compound, mp 267°-270°, [α]D20 66.3°(DMSO). NMR data was the same as for the racemic compound of Example 22.

Workup

  1. customto remove the benzyl group

Sources & evidence

ORD record
ord-1d755180d10a44618ec73b64cc0bf982
Source dataset
uspto-grants-1992_09
Patent number
US05147873

Reaction notes

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