Carbon Tetrachloride → HCID 18446626, compound

HRID 1269085Notes

Reaction equation

[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[C:14]([C:22]4[N:23]=[C:24]([CH3:27])[S:25][CH:26]=4)=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.C(Cl)(Cl)(Cl)[Cl:34]>O1CCCC1>[Cl:34][C:21]1[N:16]2[N:15]=[C:14]([C:22]3[N:23]=[C:24]([CH3:27])[S:25][CH:26]=3)[C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:12]=3)=[C:17]2[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-cyclopentyl-4-[2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyridinamine (138 mg, 0.37 mmol) in tetrahydrofuran (10 mL) was cooled to −78° C. n-Butyl lithium (1.6M in hexanes, 0.75 mL, 1.22 mmol) was added dropwise. After stirring at −78° C. for 20 minutes, carbon tetrachloride (1 mL) was added to the solution. The reaction was stirred for another 20 minutes at −78° C. and subsequently quenched with water. The reaction mixture was warmed to room temperature and extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (1:19 methanol/dichloromethane) gave 4-[7-chloro-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine as a brown oil.

Workup

additionwas added dropwise
stirringThe reaction was stirred for another 20 minutes at −78° C.
customsubsequently quenched with water
temperatureThe reaction mixture was warmed to room temperature
extractionextracted with ethyl acetate
washwashed with water, brine
dry with materialdried over magnesium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-c798285152cc4649aee24133d381be4c
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199120B2

Reaction notes

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