Acetic Acid → Benzo[1,3]dioxol-5-ylmethyl-(1h-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 1157906

반응식

HRID 1157906 반응식
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.[CH:29]1[C:34]([CH:35]=O)=[CH:33][C:32]2[O:37][CH2:38][O:39][C:31]=2[CH:30]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)Cl.FC(F)(F)C(O)=O>[O:39]1[C:31]2[CH:30]=[CH:29][C:34]([CH2:35][N:18]([CH2:17][C:9]3[NH:8][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[N:10]=3)[CH:19]3[C:28]4[N:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH2:22][CH2:21][CH2:20]3)=[CH:33][C:32]=2[O:37][CH2:38]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 8438PiperonalHCID 5049666Sodium triacetoxyborohydrideHCID 219850812-[(5,6,7,8-Tetrahydroquinolin-8-ylamino)-methyl]-benzimidazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 21985019Benzo[1,3]dioxol-5-ylmethyl-(1h-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine수율 33.1%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매HCID 8028Tetrahydrofuran용매

실험 절차

Using General Procedure B: To a solution of [1-(tert-butoxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (125 mg, 0.33 mmol), piperonal (50 mg, 0.33 mmol) and AcOH (0.02 mL, 0.33 mmol) in THF (3.3 mL) was added NaBH(OAc)3 (210 mg, 0.99 mmol) and the resultant suspension stirred at room temperature for 16 h. The crude product was dissolved in a mixture of CH2Cl2 (˜2 mL) and trifluoroacetic acid (˜2 mL). After 1.5 h, the reaction mixture was concentrated, redissolved in H2O (˜2 mL), and basified with 1N NaOH. The aqueous solution was extracted with CH2Cl2 (3×50 mL) and the combined organic extracts were dried over MgSO4 and concentrated to a yellow syrup. The product was purified by column chromatography on silica gel (100:1:1—EtOAc:MeOH:NH4OH) to give the titled compound as a white foam (45 mg, 33%). 1H NMR (300 MHz, CDCl3) δ 8.69 (d, 1H, J=3.3 Hz), 7.58 (br s, 2H), 7.43 (d, 1H, J=7.2 Hz), 7.21-7.16 (m, 3H), 6.99 (d, 1H, J=1.5 Hz), 6.79 (dd, 1H, J=8.1, 1.5 Hz), 6.65 (d, 1H, J=7.8 Hz), 5.86-5.85 (m, 2H), 4.15 (d, 1H, J=16.5 Hz), 4.09-4.06 (m, 1H), 3.98 (d, 1H, J=16.8 Hz), 3.64 (s, 2H), 2.91-2.80 (m, 1H), 2.74-2.67 (m, 1H), 2.27-2.17 (m, 1H), 2.06-1.64 (m, 2H), 1.75-1.64 (m, 1H); 13C NMR (75.5 MHz, CDCl3) δ 159.2, 158.0, 149.4, 148.7, 148.5, 139.0, 136.5, 135.0, 124.0, 123.5, 123.3, 110.7, 109.5, 102.5, 61.8, 55.5, 49.9, 31.0, 25.0, 23.1. ES-MS m/z 413.3 (M+H). Anal Calcd for (C25H24N4O2).0.8 (H2O): C, 70.34; H, 6.04; N, 13.12. Found: C, 70.29; H, 5.99; N, 12.75.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionredissolved in H2O (˜2 mL)
  3. extractionThe aqueous solution was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated to a yellow syrup
  6. customThe product was purified by column chromatography on silica gel (100:1:1—EtOAc:MeOH:NH4OH)

출처 및 근거

ORD 기록
ord-978fe8078aa54355956b804d5b7c36c3
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807694B2

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