Sodium Hydroxide → HCID 67550255, Verbindung

HRID 1071794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071794
C[O:2][C:3]([C:5]1[N:6]([CH3:35])[CH:7]=[C:8]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22](=[O:34])[NH:23][C:24]2[CH:28]=[C:27]([C:29]([O:31]C)=[O:30])[N:26]([CH3:33])[CH:25]=2)=[CH:16]3)=[O:12])[CH:9]=1)=[O:4].[OH-].[Na+]>O.CO>[OH:31][C:29]([C:27]1[N:26]([CH3:33])[CH:25]=[C:24]([NH:23][C:22]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([C:11]([NH:10][C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:35])[CH:7]=2)=[O:12])=[CH:21][CH:20]=3)=[O:34])[CH:28]=1)=[O:30]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 675501654-({1-[2-(5-methoxycarbonyl-1 methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2carboxylic acid methyl ester

Produkt 1

HCID 67550255HCID 67550255, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 4-({1-[2-(5-methoxycarbonyl-1 methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2carboxylic acid methyl ester 8 (1.04 g, 2.18 mmole) and NaOH (10 mmole) in a mixture of water/MeOH (1/4) (25 ml) was stirred at 50C for 6 h and then overnight at ambient temperature. The reaction mixture was evaporated in vacuo to dryness and the residue was dissolved in water (50 ml) and acidified with 1M HCl up to pH=3. The precipitate was collected on the filter and washed with water (3×50 ml) and dried over phosphorus pentoxide in dessicator to give 0.85 g (87%) of 4-({1-[2-(5-hydroxycarbonyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid 9 as white crystalline material. MS: 448.08 (M−H). 1H-NMR (DMSO-d6): 11.96 (s, 1H, H-1, indole); 10.45&10.25 (s&s, 1H&1H, —C(═O)NH); 8.30 (m, 1H, H-6, indole); 7.48 (m, 3H with *, H-7, indole); 7.49&7.46 (d&d, *, H-3 or H-5, Py1&Py2); 7.39 (s, 1H, H-3, indole); 6.91 (m, 2H, H-3 or H-5, Py1&Py2); 3.84&3.83 (s&s, 6H, NCH3, Py1&Py2).

Aufarbeitung

  1. customovernight
  2. customat ambient temperature
  3. customThe reaction mixture was evaporated in vacuo to dryness
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. customThe precipitate was collected on the
  6. filtrationfilter
  7. washwashed with water (3×50 ml)
  8. dry with materialdried over phosphorus pentoxide in dessicator

Quellen und Nachweise

ORD-Eintrag
ord-361a89c4bd724af99f7b93641f5ef990
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906103B2

Notizen zur Reaktion

Wird geladen…