Hydrazinecarboxylic acid, ethyl ester → HCID 136597019, compound

HRID 1476870Notes

Reaction equation

[C:1]([C:3]1[N:4]=[C:5]([O:13][C@H:14]2[C@H:18]([CH3:19])[CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[NH:27]([C:29]([O:31]CC)=O)N.C1CCN2C(=[N:38]CCC2)CC1>CN1CCCC1=O>[CH3:19][C@H:18]1[C@H:14]([O:13][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]3[NH:27][C:29](=[O:31])[NH:38][N:2]=3)[N:4]=2)[CH2:15][N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:17]1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of tert-butyl trans-3-((3-cyanoisoquinolin-1-yl)oxy)-4-methylpyrrolidine-1-carboxylate (790 mg, 2.235 mmol), ethyl hydrazinecarboxylate (1164 mg, 11.18 mmol) and DBU (168 μL, 1.118 mmol) in N-methyl-2-pyrrolidinone (5.6 mL) and under a nitrogen atmosphere was heated at 170° C. in a sealed vial for 16 hours. The reaction mixture was allowed to cool to RT and was poured onto ice water, forming a pale yellow precipitate. After the ice melted (total volume was 100 mL) the solid was filtered and dried to give the title compound as a pale yellow solid (647 mg, 70.3%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.12 (d, 3H), 1.40 (d, 9H), 3.11 (d, 1H), 3.70 (dd, 2H), 3.86-4.04 (m, 2H), 5.70-5.80 (1H, m), 7.68 (t, 1H), 7.81 (t, 1H), 7.98 (s, 1H), 8.02 (d, 1H), 8.18 (d, 1H), 11.79 (s, 1H), 12.03 (d, 1H); ESI-MS m/z [M+H-Boc]+ 312.7.

Workup

temperatureto cool to RT
additionwas poured onto ice water
customforming a pale yellow precipitate
filtrationwas filtered
customdried

Sources & evidence

ORD record: ord-0713f28d04004cfd91bb97637446393f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402841B2

Reaction notes

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