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 2417524노트

반응식

HRID 2417524 반응식
[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

참가 물질

10

반응물 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

생성물 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

시약·촉매·용매 4

HCID 702Ethanol용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a70ef332b3a04afba35b5be73ec1638e
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825191B2

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