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Acetic Acid → 4-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

HRID 2417514
ノート
印刷プレビュー

反応式

HRID 2417514 の反応式
CO[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][CH2:9][C:10]([O:12]CC)=O)=[C:5]([N+:17]([O-])=O)[CH:4]=1.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C.[H][H].[N:39]1([C:44]([C:46]2[CH:53]=[CH:52][C:49]([CH:50]=O)=[CH:48][CH:47]=2)=[O:45])[CH2:43][CH:42]=[CH:41][CH2:40]1.[C:54](O)(=[O:56])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.[OH-].[Na+].C(O)C.[Pd]>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:8]2[CH2:7][C:6]3[C:15]([O:56][CH3:54])=[CH:16][CH:3]=[CH:4][C:5]=3[N:17]([CH2:50][C:49]3[CH:52]=[CH:53][C:46]([C:44]([N:39]4[CH2:43][CH:42]=[CH:41][CH2:40]4)=[O:45])=[CH:47][CH:48]=3)[C:10](=[O:12])[CH2:9]2)=[O:26])=[CH:23][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

13

反応物 7

HCID 176Acetic AcidHCID 8471Triethylamine2 回HCID 85014-Chlorobenzoyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589883Ethyl (4-methoxy-2-nitrobenzyl)aminoacetateHCID 178418361
HCID 178418361、化合物

生成物 1

HCID 226324534-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

試薬・触媒・溶媒 5

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒5 回HCID 8857Ethyl Acetate溶媒2 回HCID 14798Sodium Hydroxide溶媒

実験手順

3.6 g (13.7 mmol) of ethyl (4-methoxy-2-nitrobenzyl)aminoacetate was dissolved in 50 ml of dichloromethane. 2.1 ml (16.4 mmol) of 4-chlorobenzoyl chloride and 2.9 ml (20.6 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was dissolved in 50 ml of ethyl acetate. 360 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction solution was filtered through Celite. The solvent was evaporated to obtain the crude product. 243 mg (0.65 mmol) of the crude product was dissolved in 5 ml of dichloromethane. 156 mg (0.78 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.074 ml (1.3 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 340 mg (1.6 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of 1 N sodium hydroxide and 10 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 131 mg (0.78 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.19 ml (1.3 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.

後処理

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. customThe solvent was evaporated
  5. customto obtain the crude product
  6. stirringwere stirred at room temperature for 30 minutes
  7. stirringwere stirred at room temperature overnight
  8. stirringthe obtained solution was stirred at room temperature for 5 hours
  9. stirringwere stirred overnight
  10. customThe solvent was evaporated
  11. customthe obtained crude product
  12. additionwas treated in the same manner as in step 3 in Example 1

出典と根拠

ORDレコード
ord-842ebded47f04d10899cde8a5c561c57
出典データセット
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06825191B2

反応ノート

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