Hydrazine hydrate (1:1) → HCID 178452588, compound

HRID 1509100Notes

Reaction equation

HRID 1509100 reaction equation
C([O:5][C:6](=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=O)[C:23](=[CH:35]N(C)C)[C:22]([CH3:40])([CH3:39])[CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.[OH2:42].[NH2:43][NH2:44]>C(O)C>[C:8]([O:42][C:6](=[O:5])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:26][C:25]4[C:24]5=[N:43][NH:44][CH:35]=[C:23]5[C:22]([CH3:39])([CH3:40])[CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:12])([CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131734398HCID 131734398, compound

Product 1

HCID 178452588HCID 178452588, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl(1-(4-(6-((dimethylamino)methylene)-7,7-dimethyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (180 mg, 0.33 mmol) in anhydrous ethanol (4 mL) was added hydrazine hydrate (48 μL, 1 mmol). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure, purified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 99:1 to 60:40) and PREP HPLC (Method A) to give the desired product as a white solid (8 mg, 5% yield). 1H NMR (500 MHz, CDCl3) 8.12 (s, 1H), 7.27-7.48 (br m, 5H), 7.25-7.18 (br m, 5H), 5.03 (br s, 1H), 3.16 (s, 2H), 2.23-2.68 (br m, 4H), 1.97-2.12 (m, 1H), 1.75-1.88 (m, 1H), 1.11-1.57 (br s, 9H+6H). LCMS (Method A): RT=6.62 min, M+H+=521.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. custompurified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 99:1 to 60:40) and PREP HPLC (Method A)

Sources & evidence

ORD record
ord-e4f63b1d255f478989be613edad39081
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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