Acetic Acid → Benzothiazol-2-yl-[1-(2-ethoxy-naphthalen-1-ylmethyl)-piperidin-4-yl]-amine

HRID 1990796

반응식

HRID 1990796 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH2:17]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[CH:30]=O)[CH3:18].C(N(C(C)C)CC)(C)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:30][C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:28]=[CH:29][C:20]=2[O:19][CH2:17][CH3:18])[CH2:13][CH2:12]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 880992-Ethoxynaphthalene-1-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14575274N-(Piperidin-4-yl)-1,3-benzothiazol-2-amine

생성물 1

HCID 86607625Benzothiazol-2-yl-[1-(2-ethoxy-naphthalen-1-ylmethyl)-piperidin-4-yl]-amine수율 8%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
40 °C

실험 절차

To a solution of benzothiazol-2-yl-piperidin-4-yl-amine (23.3 mg, 0.1 mmol, 1.0 equiv) and 2-ethoxy-naphthalene-1-carbaldehyde (commercially available, 24.0 mg, 0.12 mmol, 1.2 equiv) in ethanol (2 mL) was added diisopropylethylamine (23.42 μL, 25.9 mg, 0.2 mmol, 2.0 equiv) and acetic acid (18.0 mg, 0.3 mmol, 3.0 equiv) and the mixture stirred at 40° C. After 1 h, sodium cyano borohydride (7.54 mg, 0.12 mmol, 1.2 equiv) was added and the mixture stirred at 40° C. over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 3.3 mg (8%) of the title compound. MS (ESI): 418.4 [M+H]+.

후처리

  1. stirringthe mixture stirred at 40° C. over night
  2. customRemoval of the solvent
  3. customunder reduced pressure and purification by preparative HPLC on reversed phase
  4. washeluting with a gradient of acetonitrile/water

출처 및 근거

ORD 기록
ord-8ee5054967184bad9481d5be680ac808
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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