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

HRID 8962
Notes
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Reaction equation

HRID 8962 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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=1.57 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.

Workup

  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)

Sources & evidence

ORD record
ord-d456dfb703e64667b6df6014cffdddf0
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091217B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes