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Methanesulfonyl chloride → methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester

HRID 252980
Notes
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Reaction equation

HRID 252980 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([CH2:20][CH2:21][OH:22])[N:9]=1.C(N(C(C)C)CC)(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([CH2:20][CH2:21][O:22][S:36]([CH3:35])(=[O:38])=[O:37])[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 668410592-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethanol

Product 1

HCID 76837803methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

Compound 93, 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethanol (680 mg., 2 mmol) was dissolved in methylene chloride (10 mL) and to the reaction mixture was added diisopropylethylamine (0.6 mL, 3 mmol). The reaction was chilled to 0° C. To the reaction was added methanesulfonyl chloride (251 mg., 2.2 mmol). After fifteen minutes, the reaction was washed with saturated aqueous ammonium chloride (2×2 mL), dried with sodium sulfate, and purified by column chromatography to give Compound 95, methanesulfonic acid 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester (290 mg., 0.7 mmol).

Workup

  1. waitAfter fifteen minutes
  2. washthe reaction was washed with saturated aqueous ammonium chloride (2×2 mL)
  3. dry with materialdried with sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-218dce0d809047ff952a21757582eda0
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872005B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes