Ammonium Chloride → 3-(7-Methyl-1H-indol-3-yl)-4-[5-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-pyrrole-2,5-dione

HRID 1992634노트

반응식

HRID 1992634 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([NH2:17])=[O:16])[CH:11]=[N:12][CH:13]=2)[CH2:4][CH2:3]1.C[O:19][C:20](=O)[C:21]([C:23]1[C:31]2[C:26](=[C:27]([CH3:32])[CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>CN(C=O)C.C1COCC1.CCOC(C)=O>[CH3:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[NH:25][CH:24]=[C:23]2[C:21]1[C:20](=[O:19])[NH:17][C:15](=[O:16])[C:14]=1[C:10]1[CH:11]=[N:12][CH:13]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:9]=1

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 11241405Methyl 7-methyl-alpha-oxo-1H-indole-3-acetateHCID 23665647Potassium tert-butoxideHCID 668692842-[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetamide

생성물 1

HCID 115675473-(7-Methyl-1H-indol-3-yl)-4-[5-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-pyrrole-2,5-dione

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

2-[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetamide (150 mg, 0.64 mmol) and (7-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (209 mg, 0.96 mmol) are dissolved under an atmosphere of argon in a mixture of dry DMF (2 ml) and dry THF (2 ml). A solution of 1.0 M KOtBu in THF (1.9 ml, 1.9 mmol) is then added at RT. After 1 h at 50° C., TLC analysis indicated 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 600:115:150) to afford the title compound. 1H NMR (d6-DMSO 400 MHz): δ 2.15 (s, 3H), 2.28-2.32 (m, 2H), 2.92-3.00 (m, 2H), 3.15 (s, 3H), 6.21 (d, J=9 Hz, 1H), 6.64 (t, J=9 Hz, 1H), 6.88 (d, J=9 Hz, 1H), 7.22 (s, 1H), 7.98 (br s, 1H), 8.20-8.22 (m, 1H). ES+−MS: 402.6 [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 600:115:150)

출처 및 근거

ORD 기록
ord-64772c9654fe44949b8cecccb25e2407
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648989B2

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