Methylamine → (R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

HRID 1441378노트

반응식

HRID 1441378 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[C:15]([OH:17])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C(ON1N=NC2[CH:29]=[CH:30][CH:31]=[N:32]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>C(Cl)Cl>[CH:31]1([NH:32][C:15]([C@H:11]2[CH2:12][CH2:13][CH2:14][N:10]2[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:17])[CH2:29][CH2:30]1

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 262019311-(4-Nitrophenyl)-D-proline

생성물 1

HCID 68685984(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (R)-1-(4-nitro-phenyl)-pyrrolidine-2-carboxylic acid (Method 55; 1.8 g, 7.6 mmol) in DCM (50 ml) was added HATU (3.2 g, 8.4 mmol) and DIPEA (2.0 ml, 11.4 mmol). The reaction was stirred for 10 minutes before the addition of methylamine (0.84 g, 15 mmol); the reaction was stirred for 1 hour and then quenched with water (50 ml). The reaction was extracted with DCM (3×100 ml), dried and solvent removed in vacuo to yield a yellow gum. Purification was achieved via column chromatography eluting with 20% EtOAc/isohexane, 60% EtOAc/isohexane and finally 100% EtOAc. The title compound was obtained as a yellow solid (1.4 g, 74%). NMR (299.954 MHz, CDCl3) δ 8.13 (d, 2H), 6.55 (d, 2H), 6.06 (s, 1H), 4.14 (t, 1H), 3.70 (t, 1H), 3.38 (q, 1H), 2.75-2.66 (m, 1H), 2.36-2.29 (m, 2H), 2.17-1.95 (m, 2H), 0.82-0.73 (m, 2H), 0.46-0.35 (m, 2H); m/z 276.

후처리

  1. customquenched with water (50 ml)
  2. extractionThe reaction was extracted with DCM (3×100 ml)
  3. customdried
  4. customsolvent removed in vacuo
  5. customto yield a yellow gum
  6. customPurification
  7. washeluting with 20% EtOAc/isohexane, 60% EtOAc/isohexane and finally 100% EtOAc

출처 및 근거

ORD 기록
ord-97e50753b4884039872aaad87fd64243
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655652B2

반응 노트

불러오는 중…