Tetrahydrofuran → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-hydrazinyl-7-methylquinolin-6-yl)ethyl pivalate

HRID 931802Notes

Reaction equation

[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:41][NH2:42].C1COCC1>>[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])[C:10]1[C:11]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([NH:41][NH2:42])[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 9321Hydrazine

HCID 86691982(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate2×

Product 1

HCID 66632199(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-hydrazinyl-7-methylquinolin-6-yl)ethyl pivalate

Conditions

Temperature: 80 °C

Procedure

The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (10 mg) and hydrazine in THF (1.0 N, 1 mL, 1 mmol) was heated at 80° C. for 12 hours. Concentration under reduced pressure gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-hydrazinyl-7-methylquinolin-6-yl)ethyl pivalate, which was used for next step without purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C27H35ClN3O3: 484.2. Found: 484.3.

Workup

concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-fbb71f3117414d9c8e9128f6ec75bc23
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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