Lithium Chloride → HCID 59597387, compound

HRID 2265472Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:25][C:26]2[CH:27]=[N:28][N:29]([CH2:31][C:32](OC)=[O:33])[CH:30]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:33][CH2:32][CH2:31][N:29]1[CH:30]=[C:26]([CH2:25][N:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:27]=[N:28]1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 2-(4-{[N-(4-isopropylphenyl)-N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylcarbonyl)amino]methyl}pyrazol-1-yl)acetate (0.34 g) was dissolved in a mixed solvent (10 mL) of ethanol:THF (2:1), and sodium borohydride (0.11 g) and lithium chloride (0.12 g) were added thereto. The mixture was stirred at 50° C. for 3 hr. The reaction mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-{[1-(2-hydroxyethyl)pyrazol-4-yl]methyl}-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.23 g).

Workup

additionwere added
concentrationThe reaction mixture was concentrated under reduced pressure
custompartitioned between water and ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-85722f5a6b394093ac8a7c9f681d130a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855297B2

Reaction notes

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