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Diisopropylethylamine → 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [5-(6-fluoro-1H-benzimidazol-2-yl)-9H-pyrrolo[1,2-a]indol-9-yl]amide

HRID 1925566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1925566
C(O)(=O)C.[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:14]3[C:22]4[N:21]5[CH:23]=[CH:24][CH:25]=[C:20]5[CH:19]([NH2:26])[C:18]=4[CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[CH:27]=1.[NH:28]1[C:32]2[N:33]=[CH:34][CH:35]=[C:36]([C:37](O)=[O:38])[C:31]=2[CH:30]=[CH:29]1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:14]3[C:22]4[N:21]5[CH:23]=[CH:24][CH:25]=[C:20]5[CH:19]([NH:26][C:37]([C:36]5[C:31]6[CH:30]=[CH:29][NH:28][C:32]=6[N:33]=[CH:34][CH:35]=5)=[O:38])[C:18]=4[CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[CH:27]=1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidHCID 672997905-(6-fluoro-1H-benzimidazol-2-yl)-9H-pyrrolo[1,2-a]indol-9-ylamine acetate

Produkt 1

HCID 445378641H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [5-(6-fluoro-1H-benzimidazol-2-yl)-9H-pyrrolo[1,2-a]indol-9-yl]amideAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

A mixture of 42 mg of 5-(6-fluoro-1H-benzimidazol-2-yl)-9H-pyrrolo[1,2-a]indol-9-ylamine acetate obtained according to the preceding stage, 19 mg of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (which can be obtained according to WO 2003/000688), 39 mg of o-((ethoxycarbonyl)cyanomethylene-amino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TOTU) and 16 μl of diisopropylethylamine in 3 ml of N-methylpyrrolidone is stirred in a 100 ml round-bottomed flask. After 1 hour, the reaction medium is evaporated to dryness, the residue is taken up with 30 ml of a saturated solution of sodium bicarbonate and the aqueous phase is extracted with 4 times 30 ml of ethyl acetate. The combined organic phases are washed with 3 times 30 ml of a saturated solution of sodium chloride, dried over magnesium sulphate, and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a gradient of methanol (2% to 5% v/v) in dichloromethane, and then on a second column of silica gel (15-40 μm), elution being carried out with pure ethyl acetate. 12 mg of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [5-(6-fluoro-1H-benzimidazol-2-yl)-9H-pyrrolo[1,2-a]indol-9-yl]amide are obtained in the form of a brown solid, the characteristics of which are the following:

Aufarbeitung

  1. customobtained
  2. customthe reaction medium is evaporated to dryness
  3. extractionthe aqueous phase is extracted with 4 times 30 ml of ethyl acetate
  4. washThe combined organic phases are washed with 3 times 30 ml of a saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness under vacuum
  7. customThe residue is chromatographed on silica gel (15-40 μm), elution
  8. washon a second column of silica gel (15-40 μm), elution

Quellen und Nachweise

ORD-Eintrag
ord-c12e4a0f5cbe4cb8a417bd0a84056fab
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178687B2

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