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Ammonium Chloride → 3-(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 505239
ノート
印刷プレビュー

反応式

HRID 505239 の反応式
CC(C)([O-])C.[K+].CO[C:9](=[O:22])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH3:21])[CH:13]=1)=O.[Cl:23][C:24]1[C:25]([CH2:38][C:39]([NH2:41])=[O:40])=[CH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:34][N:35]([CH3:37])[CH3:36].[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O>[Cl:23][C:24]1[C:25]([C:38]2[C:39](=[O:40])[NH:41][C:9](=[O:22])[C:10]=2[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH3:21])[CH:13]=2)=[CH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:34][N:35]([CH3:36])[CH3:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 44536752-(1-Methyl-1H-indol-3-YL)-2-oxoacetic acid methyl esterHCID 23665647Potassium tert-butoxideHCID 668825502-(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetamide

生成物 1

HCID 594297073-(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione収率 12.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Potassium tert-butoxide (1.0 M in THF, 0.26 ml, 0.26 mmol, 3.0 equiv) was added at room temperature under an atmosphere of argon to a solution of (1-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (24 mg, 0.11 mmol, 1.3 equiv) and of crude 2-(3-chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetamide (24 mg) in anhydrous tetrahydrofuran (2.5 ml, dried over molecular sieves). The reaction mixture was stirred for 1 hour at room temperature. It was then diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. After three extractions with EtOAc, the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue via preparative HPLC afforded the title compound (4.9 mg, 4% for two steps) as its trifluoroacetate salt. 1H NMR (400 MHz, d6-DMSO): δ=11.20 (s, 1H), 8.56 (s, 1H), 8.15 (s, 1H), 8.02 (s, 1H), 8.01-7.92 (m, 1H), 7.80-7.70 (m, 1H), 7.62-7.57 (m, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.00 (t, J=7.9 Hz, 1H), 6.45 (t, J=7.5 Hz, 1H), 6.23 (d, J=8.0 Hz, 1H), 4.85-4.65 (br d, 2H), 3.87 (s, 3H), 2,85 (br s, 3H), 2.76 (br s, 3H). MS (ES+): 444 (M+H)+.

後処理

  1. extractionAfter three extractions with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue via preparative HPLC

出典と根拠

ORDレコード
ord-27fe667cfad646bbb480f712b9a67b64
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781438B2

反応ノート

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