Diisopropylethylamine → 5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 2191578Notes

Reaction equation

HRID 2191578 reaction equation
C1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][N:10](COCC[Si](C)(C)C)[C:7]3=[N:8][CH:9]=2)CC1.C([N:31]1CCC(C)(C)C(N)C1)C1C=CC=CC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:5]1[CH:4]=[CH:9][N:8]=[C:7]2[NH:10][CH:11]=[C:12]([C:13]([NH2:31])=[O:15])[C:6]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 585252801-Benzyl-4,4-dimethylpiperidin-3-amine

Product 1

HCID 866779755H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 mL flask were combined 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.45 mmol), 1-benzyl-4,4-dimethylpiperidin-3-amine (147 mg, 0.68 mmol), and HATU (188 mg, 0.50 mmol). Then added DMF (3 mL) followed by N,N-diisopropylethylamine (0.24 mL 1.35 mmol). The yellow reaction mixture was stirred at room temperature for 3 h then quenched with H2O and extracted with EtOAc (3×). The combined organics were washed with H2O (3×), dried over MgSO4 and concentrated. The crude residue was purified by SiO2 chromatography (30% to 80% EtOAc/hexanes) to afford 197 mg (82%) of N-(1-benzyl-4,4-dimethylpiperidin-3-yl)-2-cyclopropyl-5-(2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a white foam.

Workup

  1. customIn a 25 mL flask were combined
  2. customthen quenched with H2O
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with H2O (3×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude residue was purified by SiO2 chromatography (30% to 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-94b848c5adf746fe8a04416f1de3e6f7
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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