Diisopropylethylamine → 5-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamide

HRID 571545Notes

Reaction equation

HRID 571545 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH:11]1([C@@H:14]([NH2:16])[CH3:15])[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:16][C@H:14]([CH:11]2[CH2:13][CH2:12]2)[CH3:15])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4654725-Chloropyrazinoic acidHCID 7363995(S)-1-CyclopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 866757595-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamideYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloropyrazine-2-carboxylic acid (0.5 g, 3 mmol), (1S)-1-cyclopropylethanamine (0.30 g, 3.5 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.8 g, 4.7 mmol) and N,N-diisopropylethylamine (1.6 mL, 9.5 mmol) in methylene chloride (5 mL) was stirred at room temperature overnight (22 h.). The mixture was concentrated under reduced pressure. The residue was was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%) to afford the desired product (0.54 g). LCMS (M+H)+: m/z=226.1.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%)

Sources & evidence

ORD record
ord-4bdb4da925854d9dac69d029cee6add5
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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