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

HRID 1157906

反応式

HRID 1157906 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-978fe8078aa54355956b804d5b7c36c3
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

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