Hydrazine hydrate (1:1) → HCID 10185634, compound

HRID 1835351Notes

Reaction equation

HRID 1835351 reaction equation
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:6][N:7]([CH3:37])[C:8](=[O:36])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]#[C:23][CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)=[N:11][CH:10]=1.O.NN>C(O)C.COC(C)(C)C>[NH2:25][CH2:24][C:23]#[C:22][C:12]1[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:9]([C:8]([N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:45])[F:46])[CH:40]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:38]=2)[CH3:37])=[O:36])=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23502845HCID 23502845, compound

Product 1

HCID 10185634HCID 10185634, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 206 mg (0.324 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-prop-1-ynyl]-N-methyl-4-o-tolyl-nicotinamide and 0.061 ml (0.97 mmol) hydrazine hydrate (51% hydrazine) in 3.5 ml ethanol was stirred at room temperature for 1 h. The reaction mixture was diluted with tert-butyl methyl ether and washed with 1N aqueous sodium hydroxide solution. The aqueous layer was extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 93 mg (57%) of the title compound as a light brown solid.

Workup

  1. washwashed with 1N aqueous sodium hydroxide solution
  2. extractionThe aqueous layer was extracted with three portions of tert-butyl methyl ether
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4d6ac4025174db193da824ac5e72084
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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