Triethylamine → HCID 69654936, 화합물

HRID 1061362노트

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HRID 1061362 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)[OH:30].C(N(CC)CC)C.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[Cl:37][C:33]1[CH:32]=[C:31]([C@@H:29]([OH:30])[CH2:28][NH:27][CH:22]2[CH2:21][CH2:20][N:19]([C:16]3[CH:17]=[CH:18][C:13]([NH:12][S:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)(=[O:11])=[O:10])=[CH:14][CH:15]=3)[CH2:24][CH2:23]2)[CH:36]=[CH:35][CH:34]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 222205564-Methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]benzenesulfonamideHCID 56846012(1R)-2-amino-1-(3-chlorophenyl)ethan-1-ol hydrochloride

생성물 1

HCID 69654936HCID 69654936, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

A mixture of 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) (0.288 g, 0.8 mmol) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol hydrochloride (which was obtained in Example 1) (0.832 g, 4.0 mmol) was dissolved in 50 mL of methanol and the pH was adjusted to 5 with triethylamine. After stirred at room temperature for one day acetic acid (1 mL) and NaCNBH3 (50 mg, 0.8 mmol) were then added. The reaction was stirred for another day, the solvent was removed, and the residue was purified by thin layer chromatography (10% methanol/CH2Cl2) to give the title compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.60 (m, 2H), 1.95-2.10 (m, 2H), 2.50-3.10 (m, 5H), 3.50-3.70 (m, 2H), 3.79 (s, 3H), 4.80-4.90 (m, 1H), 6.79 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 7.05 (d, J=9.0 Hz, 2H), 7.30-7.50 (m, 4H), 7.60 (d, J=9.0 Hz, 2H), 9.60 (brs, 1H); MS (ES) m/z: 516.2 (MH+); HRMS Calcd. for C26H31ClN3O4S(MH+); 516.1724. Found: 516.1713.

후처리

  1. additionwere then added
  2. customthe solvent was removed
  3. customthe residue was purified by thin layer chromatography (10% methanol/CH2Cl2)

출처 및 근거

ORD 기록
ord-ab0cd0c5a55d4b9fb9347e2cf67daf69
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525202B2

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