Ammonia → HCID 22632325, compound

HRID 2417545Notes

Reaction equation

HRID 2417545 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][C:17]([C:19](O)=O)=[CH:18][C:12]=3[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:35][CH:34]=[CH:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=3)[C:10](=[O:36])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([N:41](CC)CC)C.ClC(OCC)=O.N.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][C:17]([C:19]#[N:41])=[CH:18][C:12]=3[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)=[O:30])=[CH:25][CH:24]=3)[C:10](=[O:36])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 22632627HCID 22632627, compound

Product 1

HCID 22632325HCID 22632325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.8 g (3.5 mmol) of 4-(4-chlorobenzoyl)-2-oxo-1-[4(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-2,3,4,5-tetrahydro-1H-benzo[e][1,4]-diazepine-8-carboxylic acid was dissolved in 10 ml of THF. 0.73 ml (5.3 mmol) of triethylamine and 0.40 ml (4.1 mmol) of ethyl chloroformate were added to the obtained solution, and they were stirred or 30 minutes. 10 ml of aqueous ammonia was added to the reaction mixture. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. After the treatment with ethyl acetate as the extracting solvent by ah ordinary method, the solvent was evaporated and 1.35 g (2.63 mmol) of the obtained elide product was dissolved in 20 ml of dichloromethane. 760 mg (3.19 mmol) of (methoxycarbonylsulfamoyl)-triethylammonium hydroxide was added to the obtained solution, and the obtained mixture was stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, 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. customwas elevated to room temperature
  2. stirringthe obtained mixture was stirred overnight
  3. customAfter the treatment with ethyl acetate as the extracting solvent by ah ordinary method, the solvent was evaporated
  4. dissolution1.35 g (2.63 mmol) of the obtained elide product was dissolved in 20 ml of dichloromethane
  5. stirringthe obtained mixture was stirred overnight
  6. customAfter the treatment with dichloromethane as the extracting solvent by an ordinary method, the solvent was evaporated
  7. customthe obtained crude product
  8. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-988897bd40334c6a9f1b31c2e8ccc683
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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