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

HRID 571545노트

반응식

HRID 571545 반응식
[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

참가 물질

6

반응물 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)

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-4bdb4da925854d9dac69d029cee6add5
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023840B2

반응 노트

불러오는 중…