Methyl iodide → HCID 57934820, compound

HRID 1433146Notes

Reaction equation

HRID 1433146 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([C:29]3[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:31][C:30]=3[O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[N:16][N:17]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:52]I>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([C:29]3[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:31][C:30]=3[O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[N:16][N:17]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)(=[O:20])=[O:21])[C:18]=2[CH3:52])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57934844HCID 57934844, compound

Product 1

HCID 57934820HCID 57934820, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-Butyl lithium (1.6M in hexane; 0.25 ml, 0.4 mmol) was added dropwise to a stirred, cooled (−78° C.) solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester) 240 mg, 0.33 mmol) in tetrahydrofuran (2 ml), under a nitrogen atmosphere. The mixture was stirred at −78° C. for 10 minutes, then methyl iodide (40 μL; 0.64 mmol) was added. The reaction mixture was warmed to room temperature, then partitioned between water (20 ml) and ethyl acetate (2×20 ml). The combined organic phases were dried over magnesium sulphate, then concentrated in vacuo, and purified on silica cartridge (200 mg) eluting with hexane, then hexane:diethyl ether, 1:1, then diethyl ether gave 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-methyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (70 mg; 29%)

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. custompartitioned between water (20 ml) and ethyl acetate (2×20 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. custompurified on silica cartridge (200 mg)
  6. washeluting with hexane

Sources & evidence

ORD record
ord-132d18dc37ad45bfbf775cd4e2f2772f
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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