Hydrazine hydrate (1:1) → HCID 178508029, compound

HRID 1819460Notes

Reaction equation

HRID 1819460 reaction equation
[N+:1]([C:4]1[C:5]([NH:23][CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:34][CH:33]([N:35]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:32]3)[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].O.NN>CCO.C(Cl)Cl>[NH2:35][CH:33]1[CH2:34][N:31]([C@H:28]2[CH2:29][CH2:30][C@H:25]([CH2:24][NH:23][C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([NH:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][C:19]([F:21])([F:22])[F:20])[N:6]=3)[CH2:26][CH2:27]2)[CH2:32]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57885518HCID 57885518, compound

Product 1

HCID 178508029HCID 178508029, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

2-[1-(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-azetidin-3-yl]-isoindole-1,3-dione (92 mg, 0.15 mmol) was dissolved in EtOH-CH2Cl2 (3 mL, 2:1). With stirring, hydrazine monohydrate (11.3 mg, 0.23 mmol) was added and the reaction was stirred at 25° C. for 3 h. The volatiles were removed in vacuo and the crude residue was purified via flash chromatography (SiO2, 1:9:90-NH4OH:CH3OH:CH2Cl2) to afford 46 mg (62%) of the target compound, m/z 496.35 [M+1]+.

Workup

  1. stirringthe reaction was stirred at 25° C. for 3 h
  2. customThe volatiles were removed in vacuo
  3. customthe crude residue was purified via flash chromatography (SiO2, 1:9:90-NH4OH:CH3OH:CH2Cl2)

Sources & evidence

ORD record
ord-d5af0c4c75ea4c4c94fc73e53a0ff385
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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