Sodium hydride → HCID 90387317, compound

HRID 1476839Notes

Reaction equation

HRID 1476839 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[H-].[Na+].Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([C:28]#[N:29])[N:19]=1>CN1C(=O)CCC1>[C:28]([C:20]1[N:19]=[C:18]([NH:1][CH2:2][C@@H:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:27]2[C:22]([CH:21]=1)=[CH:23][CH:24]=[CH:25][CH:26]=2)#[N:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 22250128HCID 22250128, compound

Product 1

HCID 90387317HCID 90387317, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (350 mg, 1.750 mmol) in NMP (4 mL) at 0° C. was treated with NaH (70.0 mg, 1.750 mmol) and stirred for 1 hour. Next, 1-chloroisoquinoline-3-carbonitrile (300 mg, 1.591 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-ee7b496bcde64a64ba3c7ab6d03b4714
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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