1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19005980, compound

HRID 1742948Notes

Reaction equation

HRID 1742948 reaction equation
[NH2:1][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.[N:23]1([CH:28]2[CH2:31][NH:30][CH2:29]2)[CH:27]=[N:26][CH:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:30]2[CH2:31][CH:28]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)[CH2:29]2)[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

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 675851181251925-09-3

Product 1

HCID 19005980HCID 19005980, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (75 mg, 0.25 mmol) and 100 mg (0.5 mmol) of 3-(1,2,4-triazol -1-yl)azetidine hydrochloride in 3 ml of dry pyridine, in the presence of 152 mg (1 mmol) of DBU was heated under nitrogen at 75° C. overnight. The suspension was then evaporated to dryness and to the residue water was added and solid collected, washed with water and dried to give 95 mg (94%) of the desired product as a yellow solid. m.p. 293°-295° C. 1H NMR (TFA) δ: 9.79 (s, 1H), 9.1 (s, 1H), 8.88 (s, 1H), 6.12-5.88 (m, 1H), 5.45-5.05 (m, 4H), 4.44-4.16 (m, 1H), 1.53-1.18 (m, 4H). Anal. calcd. for C18H16F2N6O3 : C, 53.74; H, 4.01; N, 20.88. Found: C, 53.60; H, 4.08; N, 20.91.

Workup

  1. customThe suspension was then evaporated to dryness and to the residue water
  2. additionwas added
  3. customsolid collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9fc0f536a08242a3b17e3daf496246e0
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

Loading…