Triethylamine → HCID 69654936、化合物

HRID 1061362ノート

反応式

HRID 1061362 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 69654936HCID 69654936、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ab0cd0c5a55d4b9fb9347e2cf67daf69
出典データセット
uspto-grants-2003_02
特許番号
US06525202B2

反応ノート

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