1-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → 8-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 743642Notes

Reaction equation

HRID 743642 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.CS(O)(=O)=O.CS(O)(=O)=O.[NH2:37][CH:38]1[CH2:41][NH:40][CH2:39]1>>[NH2:37][CH:38]1[CH2:41][N:40]([C:15]2[C:16]([F:18])=[CH:17][C:10]3[C:11]([C:14]=2[F:20])=[N:12][C:13]2[N:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7](=[O:21])[C:8]=2[CH:9]=3)[CH2:39]1

Participants

3

Reactant 2

HCID 185491641-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 19423818HCID 19423818, compound

Product 1

HCID 194237668-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 53.8%

Procedure

8-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 2, but starting with 1.3 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 1.32 g of 3-aminoazetidine dimethanesulphonate. After recrystallization in 50 cm3 of ethanol, 0.8 g of 8-(3-amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine is obtained in the form of a yellow solid, melting point 236°-238° C.

Workup

  1. custom8-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 2
  2. customAfter recrystallization in 50 cm3 of ethanol

Sources & evidence

ORD record
ord-1e5ecf662d074489b5fcbd1c38b6b52d
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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