Triethylamine → HCID 18612764, compound

HRID 1420620Notes

Reaction equation

HRID 1420620 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[NH:15][CH2:14][CH:13]2[C:23]([O-:25])=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:26](N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38]>C(Cl)Cl>[CH3:33][O:34][C:35]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:36]=1[C:37]([N:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH2:18][N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:14]1)=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 18612788HCID 18612788, compound

Product 1

HCID 18612764HCID 18612764, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 1.0 g (2.66 mmol) of 4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate from Reference Example 12 and 1.85 ml (13.3 mmol) of triethylarnine in 8 ml of CH2Cl2 was added 1.17 g (6.65 mmol) of 2,4-dimethoxybenzoyl chloride. The mixture was stirred at room temperature overnight, diluted with CH2Cl2 and washed with 2N citric acid. The organic layer was washed with H2O, 1N Na2CO3, brine and dried over Na2SO4. The solvent was removed and the residue was chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as an eluent to give 1.0 g of methyl 1-(2,4-dimethoxybenzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate as a white foam. Anal. for C27H28H2O8S: Calc'd: C,60.0; H,5.2; N,5.2; Found: C,60.0; H,5.2; N,5.1; Mass Spectrum (ES): 541.0 (M+H).

Workup

  1. washwashed with 2N citric acid
  2. washThe organic layer was washed with H2O, 1N Na2CO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customthe residue was chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as an eluent

Sources & evidence

ORD record
ord-f0f4526d51934e8aaaef11e4b1cf44f1
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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