Triethylamine → HCID 178523843, compound

HRID 258110Notes

Reaction equation

HRID 258110 reaction equation
Cl.[NH2:2][C@H:3]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[N:5]([CH2:20][C:21]2[NH:25][N:24]=[N:23][N:22]=2)[C:4]1=[O:26].C(N(CC)CC)C.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35]1[C:43](Cl)=[O:44]>ClCCl>[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35]1[C:43]([NH:2][C@H:3]1[N:9]=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[N:5]([CH2:20][C:21]2[NH:25][N:24]=[N:23][N:22]=2)[C:4]1=[O:26])=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118162081H-indole-2-carbonyl ChlorideHCID 178479292HCID 178479292, compound

Product 1

HCID 178523843HCID 178523843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

On the other hand, to a suspension of (3S)-3-amino-1,3-dihydro-5-phenyl-1-[(1H-tetrazol-5-yl) methyl]-2H-1,4-benzodiazepin-2-one hydrochloride in dry dichloromethane (50 ml) was added dropwise triethylamine (7.45 ml). To the mixture was added dropwise a solution of 2-indolylcarbonyl chloride obtained above under stirring and cooling below 10° C. After stirring under the same conditions for 2 hours, the mixture was washed with hydrochloric acid, water and brine. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give (3S)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-[(1 H-tetrazol-5-yl)-methyl]-2H-1,4-benzodiazepin-2-one (5.3 g).

Workup

  1. customobtained above
  2. temperaturecooling below 10° C
  3. stirringAfter stirring under the same conditions for 2 hours
  4. washthe mixture was washed with hydrochloric acid, water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-98635ecd8f5044e39321797167f2cd1f
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

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