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Ammonium Chloride → 3-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 1992624
ノート
印刷プレビュー

反応式

HRID 1992624 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:7][CH:8]=2)[C:3]=1[CH2:16][C:17]([NH2:19])=[O:18].C[O:21][C:22](=O)[C:23]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]([CH3:14])[CH3:15])=[CH:7][CH:8]=2)[C:3]=1[C:16]1[C:17](=[O:18])[NH:19][C:22](=[O:21])[C:23]=1[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[CH:26]=1
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 668697562-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-acetamide

生成物 1

HCID 536308903-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

Activated 3 Å molecular sieve (2.0 g) is added to a solution of 2-(2-Chloro-7-dimethylaminomethyl-naphthalen-1-yl)-acetamide (1.0 g, 3.61 mmol) and (1-Methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (1.02 g, 4.69 mmol) in dry THF (50 ml) under an atmosphere of argon. A solution of 1.0 M KOtBu in THF (10.9 ml, 10.9 mmol) is then added in one portion at RT. After 1 h at RT, TLC analysis indicates complete conversion of starting materials. The reaction mixture is diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. The organic layer is separated, washed with brine, dried over Na2SO4, and the organic solvent is evaporated. The residue is purified by FCC (EtOAc/AcOH/H2O 600:150:150) to afford the title compound, which is dissolved in glacial AcOH and lyophilized. The title compound is obtained as the water soluble bis-acetate salt. 1H NMR (d6-DMSO, 400 MHz): δ 1.80 (s, 6H), 3.20-3.42 (m, 2H), 6.10 (d, J=9.0 Hz, 1H), 6.44 (t, J=9.0 Hz, 1H), 6.94 (t, J=9.0 Hz, 1H), 7.31 (d, J=9.0 Hz, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.42 (s, 1H), 7.63 (d, J=10.8 Hz, 1H), 7.89 (d, J=9.6 Hz, 1H), 8.03 (d, J=9.0 Hz, 1H), 8.10 (s, 1H), 11.0-11.3 (br, 1H). ES+−MS: 444, 446 [M+H]+.

後処理

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe organic solvent is evaporated
  5. customThe residue is purified by FCC (EtOAc/AcOH/H2O 600:150:150)

出典と根拠

ORDレコード
ord-b1ee804370f74f2698dd2c4246233c2c
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07648989B2

反応ノート

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