Tetraethylammonium fluoride hydrate → 7-(4-Hydroxybutoxy)-8-methoxy-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

HRID 272716

Reaction equation

HRID 272716 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:38]([O:39][CH3:40])=[CH:37][C:15]2[NH:16][C:17](=[O:36])[C:18]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=4)=[CH:21][C:19]=3[NH:20][C:14]=2[CH:13]=1)(C)(C)C.[N+](CC)(CC)(CC)CC.[F-].O>C1COCC1>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:38]([O:39][CH3:40])=[CH:37][C:15]2[NH:16][C:17](=[O:36])[C:18]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=4)=[CH:21][C:19]=3[NH:20][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 16211652Tetraethylammonium fluoride hydrateHCID 692189867-[4-(Tert-butyl-dimethyl-silanyloxy)-butoxy]-8-methoxy-3-(3-methoxy-4-nitro-phenyl)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 444531387-(4-Hydroxybutoxy)-8-methoxy-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-oneYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 500A, Et4NF.H2O (10 equiv.) and THF was heated overnight at 65° C., concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by preparative HPLC to provide 50 mg (28%) of the desired product. MS (ESI) m/e 480 (M+H)+; 1H NMR (400 MHz, DMSO-d6) □ 9.63 (s, 1H), 8.01 (d, J=8.6 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 7.71 (s, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.35 (dd, J=1.5, 8.6 Hz, 1H), 7.28-7.30 (m, 2H), 6.70 (s, 1H), 6.65 (s, 1H), 4.03 (s, 3H), 3.89 (t, J=6.6 Hz, 2H), 3.67 (s, 3H), 3.44 (t, J=6.4 Hz, 2H), 1.69-1.76 (m, 2H), 1.51-1.58 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1b38afa59031419398c964c659393427
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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