Tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1h-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1h-pyrazol-3-yl]carbamate → tert-butyl [4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazo 1-2-yl]-2-hydroxypropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate

HRID 425365Notes

Reaction equation

HRID 425365 reaction equation
[CH3:1][Mg]Br.[C:4]([O:8][C:9](=[O:42])[NH:10][C:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([C:25]3[N:26]([S:35]([N:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[CH:27]=[C:28]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:29]=3)=[O:24])=[CH:18][CH:17]=2)=[CH:14][N:13]([CH3:41])[N:12]=1)([CH3:7])([CH3:6])[CH3:5]>O1CCCC1>[CH3:40][N:38]([CH3:39])[S:35]([N:26]1[CH:27]=[C:28]([CH2:30][C:31]([CH3:34])([CH3:32])[CH3:33])[N:29]=[C:25]1[C:23]([OH:24])([CH3:1])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]2[C:11]([NH:10][C:9](=[O:42])[O:8][C:4]([CH3:7])([CH3:5])[CH3:6])=[N:12][N:13]([CH3:41])[CH:14]=2)=[CH:17][CH:18]=1)(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 131729424Tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1h-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1h-pyrazol-3-yl]carbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 86637793tert-butyl [4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazo 1-2-yl]-2-hydroxypropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (3 M in diethyl ether) (0.04 mL, 0.11 mmol) was added to a 0° C. solution of tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate (32 mg, 0.06 mmol) in tetrahydrofuran (3 mL). After stirring at 0° C. for 30 min, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford tert-butyl [4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazo 1-2-yl]-2-hydroxypropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate which was used in the subsequent step without further purification.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b769928eb27d4a298170edb5e54d49af
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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