Triethylamine → HCID 7075709, compound

HRID 2202149Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=O)=[CH:4][CH:3]=1.[NH2:25][NH2:26].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[NH:26][N:25]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of tert-butyl 4-[3-(4-chlorophenyl)prop-2-ynoyl]piperidine-1-carboxylate (5.28 g, 15.18 mmol) in ethanol (160 mL) was added hydrazine (0.953 mL, 30.4 mmol) and triethylamine (4.23 mL, 30 4 mmol). The mixture was heated at 75° C. for 3 h. The solvent was evaporated under reduced pressure, and dried under vacuum to give INTERMEDIATE 1. LC-MS m/z 362.19 [M+H]+, 306.14 [M−56+H]+.

Workup

customThe solvent was evaporated under reduced pressure
customdried under vacuum

Sources & evidence

ORD record: ord-307be4d1179d44e8afe976033e51ab46
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365539B2

Reaction notes

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