Triethylamine → HCID 18612764, compound

HRID 1264607Notes

Reaction equation

HRID 1264607 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 triethylamine 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 2 N citric acid. The organic layer was washed with H2O, 1 N 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.

Workup

  1. washwashed with 2 N citric acid
  2. washThe organic layer was washed with H2O, 1 N 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-0bbc5f1dcef04a0296ea346745cab498
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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