Triethylamine → HCID 15614790, compound

HRID 620643Notes

Reaction equation

HRID 620643 reaction equation
[C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][CH:7]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:6]1=[O:34])([OH:3])=[O:2].[C:35]([O:41][CH2:42]Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>CN(C)C=O>[C:35]([O:41][CH2:42][O:2][C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:8][CH:7]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:6]1=[O:34])=[O:3])(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 14208232CCK antagonist synthetic 20

Product 1

HCID 15614790HCID 15614790, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-carboxymethyl-1,3-dihydro-3-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one (85 mg, 0.20 mmol), pivaloyloxymethylchloride (32 μl, 0.22 mmol) and triethylamine (28 μl, 0.20 mmol) was combined in 2 ml of dry dimethylformamide and allowed to stand at room temperature for 48 hours. Solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. Extractive work-up gave 100 mg of crude Product which was chromatographed on silica gel (CH3OH-CHCl3, 3:97 v/v elution) to give a white solid after trituration with ether: m.p. 225°-226° C.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customExtractive work-up gave 100 mg of crude Product which
  4. customwas chromatographed on silica gel (CH3OH-CHCl3, 3:97 v/v elution)
  5. customto give a white solid after trituration with ether

Sources & evidence

ORD record
ord-79688120b4b14035909201a7143eed02
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

Loading…