Dimethylformamide → HCID 178501055, 화합물

HRID 448963노트

반응식

HRID 448963 반응식
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.CN(C=O)C.O=P(Cl)(Cl)Cl>CC#N>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([C@H:12]3[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178501155HCID 178501155, 화합물

생성물 1

HCID 178501055HCID 178501055, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

trans-Methyl 4-({[(3-chloropyrazin-2-yl)methyl]amino}carbonyl)-cyclohexane carboxylate (29.00 g, 93.02 mmol) was dissolved in anhydrous MeCN (930 mL), anhydrous DMF (9 mL) and POCl3 (10.4 mL, 110 mmol) and heated at 55° C. under nitrogen for 3 h. The reaction mixture was concentrated in vacuo, then, the solid residue was taken up in DCM, then, basified to pH 10 with 2M ammonia in isopropanol. The mixture was concentrated in vacuo, re-dissolved in DCM, and then loaded onto TEA-basified silica gel. The crude product was purified by a silica gel column chromatography (eluted with 2:3 EtOAc/DCM) to obtain the title compound as a yellow powder; 1H NMR (CDCl3, 400 MHz) δ 1.63 (ddd, J=13.2, 13.2, 13.2, 3.2 Hz, 2H), 1.85 (ddd, J=13.2, 13.2, 13.2, 2.8 Hz, 2H), 2.10 (dd, J=14.4, 3.2 Hz, 2H), 2.19 (dd, J=14.0, 3.2 Hz, 2H), 2.46 (tt, J=12.4, 3.6 Hz, 1H), 2.96 (tt, J=11.6, 3.2 Hz, 1H), 3.70 (s, 3H), 7.33 (dd, J=5.2, 1.2 Hz, 1H), 7.61 (d, J=4.8 Hz, 1H), 7.79 (s, 1H). MS (ES+): m/z 294.17/296.14 (100/86) [MH+]. HPLC: tR=2.85 min (OpenLynx, polar—5 min).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionre-dissolved in DCM
  4. customThe crude product was purified by a silica gel column chromatography (eluted with 2:3 EtOAc/DCM)

출처 및 근거

ORD 기록
ord-b5ee0d79d43d44ac80ba20a6e13a3997
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481733B2

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