Ethylamine → 2-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246749Notes

Reaction equation

HRID 246749 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.C(N)C.CN(C(ON1N=[N:32][C:27]2[CH:28]=CC=N[C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:32][CH:27]([CH3:28])[CH3:26])=[O:13])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 866780102-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (250 mg, 1.03 mmol), ethanamine (0.2 mL 2.2 mmol) and HATU (456 mg, 1.2 mmol) in 20 mL of dry THF was stirred for 4 hours at room temperature. The reaction mixture was evaporated to dryness, the residue was suspended in 20 mL of 0.5 N HCl, product extracted with ethyl acetate (3×50 mL), organics combined dried with sodium sulfate, filtered and concentrated. Residue purified by column chromatography (silica gel, 200-300 mesh, eluting with ethyl acetate/petroleum ether 2:1) to give 2-bromo-N-isopropyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (180 mg, 43%). LCMS: (M+H)+=269/271; 1H NMR (300 MHz, CD3OD): δ 12.95 (s, 1H), 8.50 (s, 1H), 8.43 (s, 1H), 7.77-7.72 (m, 1H), 3.42-3.36 (m, 2H), 1.25-1.12 (m, 3H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionproduct extracted with ethyl acetate (3×50 mL)
  3. dry with materialorganics combined dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customResidue purified by column chromatography (silica gel, 200-300 mesh, eluting with ethyl acetate/petroleum ether 2:1)

Sources & evidence

ORD record
ord-7d639397bdcd43269bbe02c77454d465
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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