Diethanolamine → HCID 10304815, compound

HRID 2184453Notes

Reaction equation

HRID 2184453 reaction equation
[OH:1][CH:2](CO)[CH2:3][N:4]([CH3:44])[C:5]([C:7]1[N:16]2[C:10]([CH2:11][N:12]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]([F:42])([F:41])[F:40])=[C:29]([CH3:43])[CH:28]=3)=[O:26])[C:13]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:14]=3[CH2:15]2)=[CH:9][CH:8]=1)=[O:6].[O:47]=[C:48](Cl)OC(Cl)(Cl)Cl.C(N(CC)CC)C.N(CCO)CCO>ClCCl>[OH:47][CH2:48][CH2:44][N:4]([CH2:3][CH2:2][OH:1])[C:5]([C:7]1[N:16]2[C:10]([CH2:11][N:12]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]([F:41])([F:40])[F:42])=[C:29]([CH3:43])[CH:28]=3)=[O:26])[C:13]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:14]=3[CH2:15]2)=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 8113DiethanolamineHCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 10211511HCID 10211511, compound

Product 1

HCID 10304815HCID 10304815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2,3-dihydroxypropyl)-7,8-dimethoxy-N-methyl-10-{[2-methyl-2′-trifluoromethyl-[1,1′-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 18, Step D (0.31 mmol), diphosgene (1.1 equiv.) and triethylamine (1.5 equiv.) in dichloromethane (5 mL), was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (5 mL). To the solution was added triethylamine (1.5 equiv.) and diethanolamine (1.5 equiv.) and the reaction was stirred overnight. The reaction mixture was then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was first chromatographed on silica gel eluting with 2% methanol in dichloromethane and then rechromatographed with 2% methanol in ethyl acetate to provide the title compound (0.036 g) as a white solid, m.p. 130-132° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (5 mL)
  3. washThe reaction mixture was then washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was first chromatographed on silica gel eluting with 2% methanol in dichloromethane
  8. customrechromatographed with 2% methanol in ethyl acetate

Sources & evidence

ORD record
ord-751cf858ed9947f88ea16f595c71050e
Source dataset
uspto-grants-2005_05
Patent number
US06900200B2

Reaction notes

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