Sodium hydride → HCID 90386987, compound

HRID 1476798Notes

Reaction equation

HRID 1476798 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[H-].[Na+].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]([C:27]#[N:28])[N:18]=1>CN1C(=O)CCC1>[C:27]([C:19]1[N:18]=[C:17]([NH:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[C:26]2[C:21]([CH:20]=1)=[CH:22][CH:23]=[CH:24][CH:25]=2)#[N:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 22250128HCID 22250128, compound

Product 1

HCID 90386987HCID 90386987, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (S)-tert-butyl 3-aminopyrrolidine-1-carboxylate (434 mg, 2.333 mmol) in NMP (2.5 mL) at 0° C. was treated with NaH (93 mg, 2.333 mmol) and stirred for 1 hour. Next, 1-chloroisoquinoline-3-carbonitrile (400 mg, 2.121 mmol) was added and the reaction mixture was stirred at RT for 15 minutes and then heated at 140° C. for 15 minutes in a microwave reactor. The crude reaction mixture, which contained the title compound, was used without further purification. ESI-MS m/z [M+H]+ 339.4.

Workup

  1. stirringthe reaction mixture was stirred at RT for 15 minutes
  2. customThe crude reaction mixture, which

Sources & evidence

ORD record
ord-e0e5518791064d78ad4c738b6b17e7f1
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…