Hydrazine hydrate (1:1) → HCID 136374663, compound

HRID 907778Notes

Reaction equation

HRID 907778 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[C:29](=O)[C:28]3[C:27]([C:31](OC)=[O:32])=[CH:26][CH:25]=[CH:24][C:23]=3[NH:22][CH:21]2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:16][CH:15]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:42][NH2:43]>CO>[CH3:12][N:11]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[C:29]3=[N:42][NH:43][C:31](=[O:32])[C:27]4[CH:26]=[CH:25][CH:24]=[C:23]([C:28]=43)[NH:22][CH:21]2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:18][CH:19]=1)[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67261813HCID 67261813, compound

Product 1

HCID 136374663HCID 136374663, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 3-(4-(((benzyloxycarbonyl)(methyl)amino)methyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (220 mg, 0.94 mmol) in hydrazine monohydrate (50 mL) and methanol (5 mL) was stirred at 40° C. for 24 hr. The mixture was cooled to room temperature and filtered to give the crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give benzyl methyl(4-(3-oxo-8-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)benzyl)carbamate (80 mg, yield 16%). LC-MS (ESI) m/z: 517(M+1)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto give the crude product
  4. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-458ddf4eb003487988121b3e22afb6e9
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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