Dichloromethane → 2-amino-3-{4-[4-(2-carbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-propionamide hydrochloride

HRID 748984노트

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HRID 748984 반응식
C(OC(=O)[NH:7][CH:8]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:27])[NH2:26])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25](=[O:27])[NH2:26])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[C:28]([N:29]([CH3:31])[CH3:30])=[O:32]

참가 물질

3

반응물 2

HCID 6344DichloromethaneHCID 59762815(2-{4-[4-(2-Carbamoylethyl)-phenoxy]-phenyl}-1-dimethylcarbamoylethyl)-carbamic acid tert-butyl ester

생성물 1

HCID 159824562-amino-3-{4-[4-(2-carbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-propionamide hydrochloride

반응 조건

온도
2.5 °C

실험 절차

The amide compound 11 (1.5 g) was dissolved in CH2Cl2 (30 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 12 as a white amorphous solid that was extremely hygroscopic (1.0 g, 77%). 1H NMR (DMSO-d6): 7.29 (br, 1H), 7.20 (overlapped d, J=8.8 Hz, 2H), 7.19 (overlapped d, J=8.8 Hz, 2H), 6.88 (overlapped d, J=8.4 Hz, 2H), 6.87 (overlapped d, J=8.4 Hz, 2H), 6.87 (overlapped d, J=8.8 Hz, 2H), 6.76 (br, 1H), 4.63 (m, 1H), 2.83 (s, 3H), 2.54-2.78 (m, 7H), 2.34 (t, J=8.4 Hz, 2H).

후처리

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×50 mL)
  5. customdecanted
  6. customdried

출처 및 근거

ORD 기록
ord-0c5169e974e244b4b59fea8fc694b805
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

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