Dimethyl Sulfide → N-(1-(3-(Methylthio)benzyl)piperidin-3-yl)-1H-indazol-5-amine

HRID 1911890Notes

Reaction equation

CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21](=O)[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=4)[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.CSC>C1COCC1>[CH3:29][S:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[NH:5][N:6]=[CH:7]3)[CH2:16]1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a round bottom flask was added 2,2-dimethyl-1-(5-(1-(3-(methylthio)benzoyl)-piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one (240 mg, 0.655 mmol) and THF (3 mL). The solution was heated to 60° C. and borane-dimethyl sulfide complex in THF (3.0 mL of a 2.0M solution in THF, 6.0 mmol) was added, allowing dimethyl sulfide to distill off. After the starting material was consumed, the reaction was evaporated, 5N NaOH (10 mL) was added, and the mixture was extracted with EtOAc. The organic phases were dried, evaporated, and the residue was chromatographed on silica gel, eluting with 3/1-EtOAc/Heptane to afford the title compound (95 mg, 41%).

Workup

distillationto distill off
customAfter the starting material was consumed
customthe reaction was evaporated
addition5N NaOH (10 mL) was added
extractionthe mixture was extracted with EtOAc
customThe organic phases were dried
customevaporated
customthe residue was chromatographed on silica gel
washeluting with 3/1-EtOAc/Heptane

Sources & evidence

ORD record: ord-05ac4bf381be4467977a4d8fc9396c99
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604205B2

Reaction notes

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