Ammonia → 5-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid

HRID 477026Notes

Reaction equation

HRID 477026 reaction equation
[NH2:1][C:2]1([CH3:27])[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[C:15]3[C:10]([C:11](=[O:24])[C:12]([C:21]([OH:23])=[O:22])=[CH:13][N:14]3[CH:18]3[CH2:20][CH2:19]3)=[C:9](F)[C:8]=2[F:26])[CH2:3]1.[NH3:28]>>[NH2:28][C:9]1[C:8]([F:26])=[C:7]([N:4]2[CH2:5][CH2:6][C:2]([NH2:1])([CH3:27])[CH2:3]2)[C:16]([F:17])=[C:15]2[C:10]=1[C:11](=[O:24])[C:12]([C:21]([OH:23])=[O:22])=[CH:13][N:14]2[CH:18]1[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 14304602HCID 14304602, compound

Product 1

HCID 157293795-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(3-amino-3-methyl-1-pyrrolidinyl)-1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (150 mg) and 28% aqueous ammonia (15 ml) was heated at 100° C. for 48 hours in a sealed tube. The reaction mixture was evaporated to dryness under reduced pressure and water was added to the residue. The resulting crystals were treated in the same manner as described in Example 10 (1) to give 5-amino7-(3-amino-3-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (93 mg), m.p. 271°-273° C (decomp.).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure and water
  2. additionwas added to the residue
  3. additionThe resulting crystals were treated in the same manner

Sources & evidence

ORD record
ord-21fb80f8f9384f09a84f946faa05538b
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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