Triethylamine → 1-[4-(1-Pyrrolidinecarbonyl)benzyl]-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo-[e][1,4]diazepin-2-on

HRID 2417474Notes

Reaction equation

HRID 2417474 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][N:12]([C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:11][C:10]2=[O:29])=[CH:6][CH:5]=1)([OH:3])=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C(N(CC)CC)C>ClCCl>[N:32]1([C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][N:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[CH2:13][N:12]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[CH2:11][C:10]3=[O:29])=[CH:30][CH:31]=2)=[O:3])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 226325341-(4-Carboxybenzyl)-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Product 1

HCID 226324151-[4-(1-Pyrrolidinecarbonyl)benzyl]-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo-[e][1,4]diazepin-2-on

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23 mg (0.053 mmol) of 1-(4-carboxybenzyl)-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on was dissolved in 5 ml of dichloromethane. 6 mg (0.079 mmol) of pyrrolidine, 13 mg (0.079 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.022 ml (0.159 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe obtained crude product
  3. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-dcfba47f431046bb94f1084f54394fba
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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