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Diisopropylethylamine → HCID 58727774, compound

HRID 1992121
Notes
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Reaction equation

HRID 1992121 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]([CH:9]2[CH2:15][CH:14]3[N:16]([CH2:17][CH2:18][C:19]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[C:7]2[CH:31]=[CH:32][CH:33]=[CH:34][C:6]=2[N:5]=1.[C:35](=O)([O:45]C1C=CC([N+]([O-])=O)=CC=1)[O:36][C@@H:37]1[C@H:44]2[C@H:40]([O:41][CH2:42][CH2:43]2)[O:39][CH2:38]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:3][C:4]1[N:8]([CH:9]2[CH2:15][C@H:14]3[N:16]([CH2:17][CH2:18][C:19]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:20][CH2:21][N:22]([C:35]([O:36][C@@H:37]5[C@H:44]6[C@H:40]([O:41][CH2:42][CH2:43]6)[O:39][CH2:38]5)=[O:45])[CH2:23][CH2:24]4)[C@H:11]([CH2:12][CH2:13]3)[CH2:10]2)[C:7]2[CH:31]=[CH:32][CH:33]=[CH:34][C:6]=2[N:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11266393(3R,3αS,6αR)-Hexahydrofuro[2,3-β]furan-3-yl-4-nitrophenyl carbonateHCID 686757782-methyl-1-{8-[2-(4-phenyl piperidin-4-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole dihydrochloride

Product 1

HCID 58727774HCID 58727774, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of 2-methyl-1-{8-[2-(4-phenyl piperidin-4-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole dihydrochloride (100 mg, 0.22 mmol), (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate (78 mg, 0.26 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.88 mmol) in acetonitrile (3 mL) was stirred at rt for 16 h. The reaction mixture was concentrated and the residue in dichloromethane was washed with saturated sodium carbonate solution, dried, concentrated and chromatographed on silica gel eluting with 1:40 methanol:dichloromethane to give (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboxylate as a clear glass (0.064 g, 50%). 1H NMR (400 MHz, CDCl3) δ 7.38 (m, 2H), 7.29 (m, 5H), 7.16 (m, 2H), 5.71 (m, 1H), 5.18 (m, 1H), 4.59 (m, 1H), 3.75-4.04 (m, 7H), 3.22 (m, 3H), 3.05 (m, 1H), 2.58 (m, 3H), 2.19-2.36 (m, 4H), 1.80-1.92 (m, 9H), 1.61 (m, 5H). HRMS C35H44N4O4 m/z 585.3441 (M+H)Cal., 585.3440 (M+H)Obs..

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue in dichloromethane was washed with saturated sodium carbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with 1:40 methanol

Sources & evidence

ORD record
ord-bddc4977e0fa4d52a36a7207829bc0f5
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07645771B2

Reaction notes

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