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

HRID 2363353노트

반응식

HRID 2363353 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-c075b0a390494c879de2b9cecdefda5f
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691807B2

반응 노트

불러오는 중…