Hydrazine hydrate (1:1) → 7-Fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one

HRID 1968160Notes

Reaction equation

HRID 1968160 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:25](OCC)=[O:26])[C:5]2[C:6](=O)[CH:7]([C:18]3[N:22]([CH3:23])[N:21]=[CH:20][N:19]=3)[CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][C:10]=2[CH:11]=1.O.[NH2:31][NH2:32]>CO>[F:1][C:2]1[CH:11]=[C:10]2[NH:9][CH:8]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:7]([C:18]3[N:22]([CH3:23])[N:21]=[CH:20][N:19]=3)[C:6]3=[N:31][NH:32][C:25](=[O:26])[C:4]([CH:3]=1)=[C:5]23

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260859Ethyl 7-fluoro-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1359243497-Fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-oneYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 7-fluoro-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (186 mg, 0.47 mmol) in methanol (1 mL) was added hydrazine monohydrate (0.5 mL), and the mixture was stirred at 25° C. for 15 hr. Then the mixture was filtered to obtain a white solid (40 mg, yield 24%). LC-MS (ESI) m/z: 363 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.63 (s, 3H), 4.94-5.03 (m, 2H), 6.91-6.94 (dd, J1=11.6 Hz, J2=2.4 Hz, 1H), 7.05-7.08 (dd, J1=9.6 Hz, J2=2.4 Hz, 1H), 7.29-7.35 (m, 3H), 7.42-7.48 (m, 2H), 7.74 (s, 1H), 7.79 (s, 1H), 12.34 (s, 1H).

Workup

  1. filtrationThen the mixture was filtered

Sources & evidence

ORD record
ord-f8eaa9fd6d35479e91eeff4c2e3cbed4
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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