Acetic Acid → 4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]-diazepin-2-on

HRID 2417524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417524
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:3]=1[CH2:4][N:5]([CH2:15][C:16](OCC)=[O:17])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[N:27]1([C:32]([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)=[O:33])[CH2:31][CH:30]=[CH:29][CH2:28]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCl.[OH-].[Na+].C(O)C.C(OCC)(=O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([N:5]2[CH2:4][C:3]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:2]=3[N:1]([CH2:38][C:37]3[CH:36]=[CH:35][C:34]([C:32]([N:27]4[CH2:31][CH:30]=[CH:29][CH2:28]4)=[O:33])=[CH:41][CH:40]=3)[C:16](=[O:17])[CH2:15]2)=[O:14])=[CH:12][CH:11]=1

Komponenten

10

Edukt 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589885Ethyl [(2-amino-5-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

Produkt 1

HCID 226326524-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]-diazepin-2-on

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

320 mg (0.85 mmol) of ethyl [(2-amino-5-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate was dissolved in 5 ml of dichloromethane. 205 mg (1.0 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.097 ml (1.7 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 440 mg (2.1 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 5 ml of 1 N sodium hydroxide and 5 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. 169 mg (1.0 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.24 ml (1.7 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.

Aufarbeitung

  1. stirringwere stirred at room temperature overnight
  2. stirringthe obtained solution was stirred at room temperature for 5 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated
  5. customthe obtained crude product
  6. additionwas treated in the same manner as in step 3 in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-a70ef332b3a04afba35b5be73ec1638e
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825191B2

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