Triethylamine → HCID 178424284、化合物

HRID 1979321ノート

反応式

HRID 1979321 の反応式
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:11]=[C:12]([C:16]2[NH:20][N:19]=[N:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.[C:33]1([CH3:61])[C:34]([C:39]([CH2:41][N:42]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[N:46]([C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:45][CH:44]([NH2:59])[C:43]2=[O:60])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[C:33]1([CH3:61])[C:34]([C:39]([CH2:41][N:42]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[N:46]([C:53](=[O:58])[C:54]([CH3:56])([CH3:57])[CH3:55])[CH2:45][CH:44]([NH:59][C:22]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]4[NH:20][N:19]=[N:18][N:17]=4)[CH:11]=3)=[O:24])[C:43]2=[O:60])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1

参加物

8

反応物 4

HCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 212016481-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 212019913-(2H-tetrazol-5-yl)-phenylamine hydrochloride

生成物 1

HCID 178424284HCID 178424284、化合物収率 144.2%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Triethylamine (0.44 ml) was added to a suspension of 5-(3-aminophenyl)tetrazole hydrochloride (prepared according to International Publication WO93/17011) (316 mg) in anhydrous tetrahydrofuran (10 ml). After cooled at 0° C., triphosgene (157 mg) was added, and the mixture was adjusted to pH 8 with triethylamine (0.22 ml). After returned at room temperature, stirred for 30 minutes, 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (472 mg) obtained from Step 3 of Example 1 in anhydrous tetrahydrofuran (10 ml) was added to the reaction mixture, and then stirred at room temperature for one hour. Ethyl acetate (20 ml) was added to the resultant mixture, 10% acetic acid (20 ml) was added thereto and separated into organic layer and aqueous layer. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=5:1) and the mixed solvent of isopropyl ether and ethanol was added to the residue for trituration, collected by filtration, to thereby obtain 443 mg of the title compound (Yield: 63.6%) as white powder.

後処理

  1. customAfter returned at room temperature
  2. stirringstirred at room temperature for one hour
  3. additionwas added
  4. customseparated into organic layer and aqueous layer
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)
  8. additionthe mixed solvent of isopropyl ether and ethanol was added to the residue for trituration
  9. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-e84f9def7b684e72b5be87ee5be9a19c
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

読み込み中…