1-Methyl-1H-indole-2-carbonyl chloride → N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide

HRID 1270918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270918
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[C:16]([I:17])[C:11]=3[O:10][CH:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[C:31](Cl)=[O:32]>N1C=CC=CC=1>[NH2:18][C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:31]([C:23]4[N:22]([CH3:21])[C:30]5[C:25]([CH:24]=4)=[CH:26][CH:27]=[CH:28][CH:29]=5)=[O:32])=[C:3]([O:19][CH3:20])[CH:4]=3)=[CH:9][O:10][C:11]=2[C:16]([I:17])=[CH:15][N:14]=1

Komponenten

4

Edukt 2

HCID 123033141-Methyl-1H-indole-2-carbonyl chlorideHCID 184507093-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine

Produkt 1

HCID 18451296N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamideAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-(4-amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine (2.53 g, 6.65 mmol) in pyridine (30 mL) was cooled to 0° C. and 1-methyl-1H-2-indolecarbonyl chloride (2.57 g, 13.3 mmol) was added. The mixture was stirred for 15 minutes at 0° C. and then allowed to rise to ambient temperature over an 18 hour time period. The solvent was removed in vacuo and the residue was dissolved in water (50 mL) and brought to pH 12 with 0.1 N aqueous sodium hydroxide, at which point a precipitate formed. The suspension was extracted with dichloromethane (4×25 mL) and the combined organic layers were washed with brine (25 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title compound (3.21 g, 89%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.48 (s, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 8.04 (t, 1H), 7.71 (d, 1H), 7.59 (d, 1H), 7.30–7.37 (m, 2H), 7.25 (d, 1H), 7.11–7.18 (m, 2H), 5.75–5.83 (bs, 2H), 4.04 (s, 3H), 3.93 (s, 3H); RP-HPLC (Conditions d) Rt 8.73 min.; MS: MH+ 539.

Aufarbeitung

  1. waitto rise to ambient temperature over an 18 hour
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in water (50 mL)
  4. customformed
  5. extractionThe suspension was extracted with dichloromethane (4×25 mL)
  6. washthe combined organic layers were washed with brine (25 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8703f89ccc9442aa45c090ccfe10a5b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202363B2

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