Triethylamine → (S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride

HRID 727265

反応式

HRID 727265 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@H:10]([CH2:24][C:25]([OH:27])=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.CN(CCCN=C=NCC)C.C(N(CC)CC)C.[NH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>CN(C)C=O.O>[ClH:1].[N:50]1[CH:51]=[CH:52][CH:53]=[C:48]([NH:47][C:25](=[O:27])[CH2:24][C@@H:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]23)[CH:49]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

生成物 1

HCID 68971820(S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride収率 52.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(S)-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (2.64 g) is dissolved in dimethylformamide (30 ml). N-Dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride (1.51 g) and triethylamine (1.08 ml) are added in order and the mixture is stirred. Five minutes later, 3-aminopyridine (0.66 g) is added to the reaction mixture and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water, and the obtained crystals are purified by column chromatography (chloroform: methanol =50: 1). The crystals are converted to hydrochloride with ethanol/hydrochloric acid in ethyl acetate, and recrystallized from ethanol/ethyl acetate to give 0.88 g of (S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride, melting point 198°-201° C.

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. customthe obtained crystals are purified by column chromatography (chloroform: methanol =50: 1)
  3. customrecrystallized from ethanol/ethyl acetate

出典と根拠

ORDレコード
ord-978999084ac34d5d9bb2ea0de67d2ed0
出典データセット
uspto-grants-1998_01
特許番号
US05712274

関連ノート

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