Triethylamine → methyl 1-(4-ethoxybenzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1264605Notes

Reaction equation

HRID 1264605 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][CH3:26])=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:27]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH3:28].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:27]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:15]2[C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[CH2:18][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:10])=[O:11])[CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:14]2)=[O:35])=[CH:32][CH:31]=1)[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1400594-Ethoxybenzoyl ChlorideHCID 18612753Methyl 4-(4-Methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

Product 1

HCID 18612807methyl 1-(4-ethoxybenzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5tetrahydro-1H-[1,4]benzodiazepine-3-carboxylateYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.270 g of methyl 4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate of Reference Example 12, 0.291 g of 4-ethoxybenzoyl chloride and 500 μl of triethylamine in 5 ml of CH2Cl2 was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and H2O and the CH2Cl2 layer was separated and concentrated to dryness. The residue was triturated with ethyl acetate to give 0.276 g of methyl 1-(4-ethoxybenzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate as white crystals, mp 187-190° C.

Workup

  1. customthe CH2Cl2 layer was separated
  2. concentrationconcentrated to dryness
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-6285ce612cdb4027add3372537cf6e92
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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