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

HRID 246739Notes

Reaction equation

HRID 246739 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][CH:15]([NH2:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=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:17][CH:15]([CH3:16])[CH3:14])=[O:13])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 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 62%

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), propan-2-amine (0.15 mL, 1.5 mmol) and HATU (456 mg, 1.2 mmol) in 20 mL of dry THF was stirred for 4 hours. 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 were dried with sodium sulfate and concentrated. The residue was 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, 62%). 1H NMR (300 MHz, DMSO): δ 12.95 (s, 1H), 8.49 (s, 1H), 8.43 (s, 1H), 7.59-7.56 (m, 1H), 4.13-4.06 (m, 1H), 1.24-1.20 (m, 6H). LCMS: (M+H)+=283/285.

Workup

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

Sources & evidence

ORD record
ord-bf67b1aa8cd846129d25c7a88a017e81
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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