Aluminium lithium hydride → 4-[3-(Cyclopropylmethyl-amino)-pyrazol-1-yl]-benzylamine

HRID 1191096Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][NH:11][C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:13]=2)[CH2:9][CH2:8]1>C1COCC1>[CH:7]1([CH2:10][NH:11][C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=3)[N:13]=2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

Add a solution of 1M lithium aluminum hydride in THF (1.4 mL, 1.4 mmol) to a solution of 4-[3-(cyclopropylmethyl-amino)-pyrazol-1-yl]-benzonitrile (136 mg, 0.57 mmol) in THF (10 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 1 h at 60° C. Cool the mixture to room temperature and quench slowly with water, 1N NaOH and additional water. Dilute with EtOAc, stir vigorously for 20 min and filter through Celite®. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the residue by SCX chromatography to obtain the desired intermediate that was used without further purification (130 mg, 94%). MS (ES+) m/z: 243 (M+H)+.

Workup

temperatureCool the mixture to room temperature
customquench slowly with water, 1N NaOH and additional water
additionDilute with EtOAc
stirringstir vigorously for 20 min
filtrationfilter through Celite®
dry with materialDry the organic phase over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customPurify the residue by SCX chromatography

Sources & evidence

ORD record: ord-5ad73e95a6f5491e8b31c26903741522
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680091B2

Reaction notes

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