Sodium hydride → HCID 90387389, compound

HRID 1476795Notes

Reaction equation

HRID 1476795 reaction equation
[OH: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]([O: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 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 22250128HCID 22250128, compound

Product 1

HCID 90387389HCID 90387389, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (496 mg, 2.65 mmol) in NMP (4 mL) at 0° C. was treated with NaH (106 mg, 2.65 mmol) and stirred for 1 hour. Next, 1-chloroisoquinoline-3-carbonitrile (500 mg, 2.65 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 directly in the next step.

Workup

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

Sources & evidence

ORD record
ord-56785477bfa147a086a3f078861ac630
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…