5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 19006008, compound

HRID 1742966Notes

Reaction equation

HRID 1742966 reaction equation
N[C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.C([O:25][C:26]([C:28]1[N:32]([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[N:31]=[N:30][CH:29]=1)=[O:27])C.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>>[CH:15]1([N:7]2[C:8]3[C:3](=[CH:2][C:11]([F:12])=[C:10]([N:35]4[CH2:36][CH2:37][CH:33]([N:32]5[C:28]([C:26]([OH:27])=[O:25])=[CH:29][N:30]=[N:31]5)[CH2:34]4)[C:9]=3[F:14])[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6]2)[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19005973HCID 19005973, compoundHCID 57346892Diazabicycloundecane

Product 1

HCID 19006008HCID 19006008, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.33 mmol), 3-(5-ethoxycarbonyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (178 mg, 0.83 mmol) and diazabicycloundecane (127 mg, 0.83 mmol) was heated at 110° C. for 24 hrs. The mixture was concentrated, diluted with water and the separated solid was washed with water and acetonitrile. The solid was dried in air and redissolved in methanol (5 ml) and to it NaOH (20 mg) in water (5 ml) was added. The solution was heated at 90° C. for 6 hrs., cooled and pH lowered using 1N HCl to 4. The separated solid was filtered, recrystallized from methanol/ether, yield 20 mg (13.98%), m.p. 214° C. 1H NMR (TFA) δ: 1.30-1.62 (m, 4H), 2.70-3.0 (m, 2H), 3.74-4.80 (m, 5H), 5.60-5.70 (m, 1H), 8.86 (s, 1H), 9.14 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. washthe separated solid was washed with water and acetonitrile
  4. customThe solid was dried in air
  5. dissolutionredissolved in methanol (5 ml) and to it NaOH (20 mg) in water (5 ml)
  6. additionwas added
  7. temperatureThe solution was heated at 90° C. for 6 hrs
  8. temperature, cooled
  9. filtrationThe separated solid was filtered
  10. customrecrystallized from methanol/ether, yield 20 mg (13.98%), m.p. 214° C

Sources & evidence

ORD record
ord-1437bbf1136e46679df609b825629fb0
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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