tert-Butyl isocyanate → HCID 66585082, compound

HRID 589845Notes

Reaction equation

HRID 589845 reaction equation
[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[C:4]([C:11]#[N:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([N:23]=[C:24]=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([NH:23][C:24]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([Cl:1])=[C:3]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:4]([C:11]#[N:12])=[C:5]2[CH2:10]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 66585081HCID 66585081, compound

Product 1

HCID 66585082HCID 66585082, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 34 g (119 mmol) of 6-chloro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carbonitrile in 300 ml of dichloromethane are added 16.3 ml (143 mmol) of tert-butyl isocyanate (CAS1609-86-5). After stirring for 4 hours at room temperature, the solvent is evaporated off under reduced pressure to give an orange-coloured solid, which is crystallized from acetonitrile to give 40.0 g of N-tert-butyl-6-chloro-8-cyano-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide in the form of a yellow powder after filtering off and drying.

Workup

  1. customthe solvent is evaporated off under reduced pressure
  2. customto give an orange-coloured solid, which
  3. customis crystallized from acetonitrile

Sources & evidence

ORD record
ord-58e2c9df27f54bb1a51e3d00ae0fa774
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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