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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 2417511
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HRID 2417511 반응식
[NH2:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[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[C:21]([O:25][CH3:26])=[CH:22][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
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참가 물질

10

반응물 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589882Ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

생성물 1

HCID 22632453
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

시약·촉매·용매 4

HCID 702Ethanol용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

243 mg (0.65 mmol) of ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate 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-dimethyl-imidazonium 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.

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-98c0980a289a4b51b5acf63288ce4e42
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06825191B2

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