Tert-Butylamine → 2-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246713Notes

Reaction equation

HRID 246713 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([OH:13])=O)=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.[CH3:14][C:15]([NH2:18])([CH3:17])[CH3:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:18][C:15]([CH3:17])([CH3:16])[CH3:14])=[O:13])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 866779952-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (0.2 g, 0.83 mmol), 2-methylpropan-2-amine (66 mg, 0.91 mmol), EDCI (476 mg, 2.49 mmol) and HOBt (112 mg, 0.83 mmol) in dry dichloromethane (20 mL) was stirred at room temperature for 16 hours. Reaction mixture was concentrated to about half the volume and the formed precipitate was separated by filtration, the filter cake was washed with dichloromethane and dried to afford 2-bromo-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (103 mg, 42%) as a yellow solid. LCMS: (M+H)+=297.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated to about half the volume
  3. customthe formed precipitate was separated by filtration
  4. washthe filter cake was washed with dichloromethane
  5. customdried

Sources & evidence

ORD record
ord-380c1752d696427f883a186be3b869eb
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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