Hydrochloric Acid → 1-(9-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)-4-phenethylpiperazin-2-one hydrochloride

HRID 2365388노트

반응식

HRID 2365388 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:9]=2)[C:4]2[CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][C:3]1=2.[ClH:37]>CO.CCOCC>[ClH:37].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:9]=2)[C:4]2[CH2:26][CH2:27][NH:28][CH2:29][C:3]1=2

참가 물질

5

반응물 2

HCID 313Hydrochloric Acid2회HCID 67986813tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

생성물 1

HCID 679695921-(9-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)-4-phenethylpiperazin-2-one hydrochloride수율 33%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매2회

실험 절차

tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (35 mg, 0.071 mmol) was dissolved in MeOH (2 mL), and 2 N HCl in Et2O (10 mL) was added. The reaction was allowed to proceed for 18 h. The mixture was concentrated, and the residue was partitioned between CH2Cl2 and sat. Na2CO3 solution. The organic phase was removed, and the aqueous phase was back extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was dissolved in MeOH (1 mL), treated with 2 N HCl in Et2O (12 μL, 0.024 mmol), and concentrated to provide the title compound (10 mg, 33%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.60 (d, J=8.3 Hz, 1H), 7.45 (s, 1H), 7.41-7.34 (m, 4H), 7.33-7.27 (m, 1H), 7.67 (d, J=8.2 Hz, 1H), 4.54 (s, 2H), 4.24-4.15 (m, 2H), 4.15-4.03 (m, 2H), 3.91-3.76 (m, 2H), 3.72 (s, 3H), 3.61-3.54 (m, 4H), 3.22-3.16 (m, 2H), 3.14-3.08 (m, 2H); ESI MS m/z 389 [M+H]+; HPLC (Method B) 94.4% (AUC), tR=10.2 min.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and sat. Na2CO3 solution
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was back extracted with CH2Cl2
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue was dissolved in MeOH (1 mL)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4aa9eb9cd51d41a28a8c883544d5391c
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697700B2

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