Water → Ethyl 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 246976Notes

Reaction equation

HRID 246976 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:8][CH2:7][NH:6][CH2:5]1.C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N:24]1[C:33]2[C:28](=[CH:29][C:30]([F:51])=[C:31](OP(OC3C=CC=CC=3)(OC3C=CC=CC=3)=O)[N:32]=2)[C:27](=[O:52])[C:26]([C:53]([O:55][CH2:56][CH3:57])=[O:54])=[CH:25]1.O>C(O)C>[NH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:31]2[N:32]=[C:33]3[C:28]([C:27](=[O:52])[C:26]([C:53]([O:55][CH2:56][CH3:57])=[O:54])=[CH:25][N:24]3[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[F:16])=[CH:29][C:30]=2[F:51])[CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13849344Ethyl 1-(2,4-difluorophenyl)-7-diphenoxyphosphinyloxy-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateHCID 162125963-Aminopyrrolidine dihydrochloride

Product 1

HCID 13667039Ethyl 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylateYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2 ml of ethanol was suspended 64 mg of 3-aminopyrrolidine dihydrochloride, and 130 mg of triethylamine was added to the resulting suspension to form a solution. Subsequently, 200 mg of ethyl 1-(2,4-difluorophenyl)-7-diphenoxyphosphinyloxy-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate was added to the solution, and the resulting mixture was subjected to reaction at room temperature of 1 hour. Subsequently, 3 ml of water was added to the reaction mixture, and the crystals thus deposited were collected and washed with 3 ml of water to obtain 110 mg (yield 75.9%) of ethyl 7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate. The physical properties of this compound were identical with those of the compound obtained in Example 64.

Workup

  1. additionwas added to the resulting suspension
  2. customto form a solution
  3. customthe resulting mixture was subjected to reaction at room temperature of 1 hour
  4. customthe crystals thus deposited were collected
  5. washwashed with 3 ml of water

Sources & evidence

ORD record
ord-7f168785e74448a690995fd57dec24fd
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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