Acetic Acid → 6-chloro-4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-7-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]-diazepin-2-on

HRID 2417502ノート

反応式

HRID 2417502 の反応式
[NH2:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[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:26]1([C:31]([C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=2)=[O:32])[CH2:30][CH:29]=[CH:28][CH2:27]1.[C:41](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.Cl.O1CCOCC1.C(OCC)(=O)C>[Cl:25][C:21]1[C:3]2[CH2:4][N:5]([C:6](=[O:14])[C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=3)[CH2:15][C:16](=[O:17])[N:1]([CH2:37][C:36]3[CH:39]=[CH:40][C:33]([C:31]([N:26]4[CH2:30][CH:29]=[CH:28][CH2:27]4)=[O:32])=[CH:34][CH:35]=3)[C:2]=2[CH:24]=[CH:23][C:22]=1[CH3:41]

参加物

12

反応物 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589878Ethyl [(2-amino-6-chlorobenzyl)-(4-chlorobenzoyl)amino]acetate

生成物 1

HCID 226324016-chloro-4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-7-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]-diazepin-2-on

試薬・触媒・溶媒 6

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒HCID 312751,4-Dioxane溶媒

実験手順

140 mg (0.37 mmol) of ethyl [(2-amino-6-chlorobenzyl)-(4-chlorobenzoyl)amino]acetate and 89 mg (0.44 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde were dissolved in 5 ml of dichloromethane. 0.042 ml (0.74 mmol) of acetic acid was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 195 mg (0.93 mmol) of sodium triacetoxyborohydride was added to the obtained solution, 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 they were stirred at room temperature for 4 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. 74 mg (0.44 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.1 ml (0.74 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated and the obtained crude product was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane. The obtained solution was stirred at room temperature for 3 hours. 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. stirringwere stirred at room temperature overnight
  2. stirringwere stirred at room temperature for 4 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated
  5. customthe obtained crude product
  6. stirringThe obtained solution was stirred at room temperature for 3 hours
  7. customThe solvent was evaporated
  8. customthe obtained crude product
  9. additionwas treated in the same manner as in Step 3 in Example 1

出典と根拠

ORDレコード
ord-f9d3cb2c9d2b44eeafc106ba885d5aed
出典データセット
uspto-grants-2004_11
特許番号
US06825191B2

反応ノート

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