Hydrazine hydrate (1:1) → HCID 136374714, compound

HRID 907925Notes

Reaction equation

HRID 907925 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]2[CH:21]([C:22]3[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=3)[C:20](=O)[C:19]3[C:18]([C:29]([O:31]CC)=O)=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13]2)[CH:8]=[CH:9][C:10]=1[F:11])=[O:4].O.[NH2:36][NH2:37]>CO>[F:11][C:10]1[CH:9]=[CH:8][C:7]([CH:12]2[NH:13][C:14]3[C:19]4[C:20](=[N:36][NH:37][C:29](=[O:31])[C:18]=4[CH:17]=[CH:16][CH:15]=3)[CH:21]2[C:22]2[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=2)=[CH:6][C:5]=1[C:3]([N:2]([CH3:1])[CH3:34])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67259096HCID 67259096, compound

Product 1

HCID 136374714HCID 136374714, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound ethyl 2-(3-(dimethylcarbamoyl)-4-fluorophenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (130 mg) in hydrazine monohydrate (85%, 2 mL) and methanol (5 mL) was stirred at room temperature for 4 h. The resulting mixture was filtered and washed with water (20 ml) and methanol (5 ml) to obtain a white solid. The solid was dried in vacuum at 50° C. to obtain the title compound (30.0 mg, yield 30%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.72 (s, 3H), 2.97 (s, 3H), 3.43 (s, 3H), 4.67-4.70 (d, J=10.8 Hz, 1H), 4.95-4.97 (d, J=10.8 Hz, 1H), 6.72-6.73 (d, J=1.2 Hz, 1H), 6.89-6.89 (d, J=0.8 Hz, 1H), 7.15-7.23 (m, 2H), 7.34-7.41 (m, 3H), 7.48-7.49 (m, 1H), 7.56-7.60 (t, J=8 Hz, 1H), 12.17 (s, 1H); LC-MS (ESI) m/z: 433 (M+1)+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with water (20 ml) and methanol (5 ml)
  3. customto obtain a white solid
  4. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-d9f9882b9e9e462396df522eb2c55087
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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