Chloromethyl Methyl Ether → HCID 67464142, compound

HRID 1907137Notes

Reaction equation

HRID 1907137 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][NH:13][N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[CH2:44][O:45][CH3:46]>C1COCC1>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][N:13]([CH2:44][O:45][CH3:46])[N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 178492656HCID 178492656, compound

Product 1

HCID 67464142HCID 67464142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2H-indazole-7-carboxylic acid isopropylamide (500 mg, 1.07 mmol) and diisopropylethylamine (225 μL, 1.2 mmol) in THF (10 mL) was treated dropwise with chloro-methoxy-methane (90 μL, 1.2 mmol). The resulting reaction mixture was stirred for 2 hours at ambient temperature. The reaction mixture was concentrated in vacuo. Purification of the residue by flash-chromatography (SiO2, CH2Cl2/acetone 7:3) afforded the title compound as a colorless crystalline solid. M.p. 148° C., LC/MS:512/514 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customPurification of the residue by flash-chromatography (SiO2, CH2Cl2/acetone 7:3)

Sources & evidence

ORD record
ord-1cdf99082f43436785d4964c83502195
Source dataset
uspto-grants-2013_12
Patent number
US08598078B2

Reaction notes

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