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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
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HRID 1992624 반응식
[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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b1ee804370f74f2698dd2c4246233c2c
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07648989B2

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