Diisopropylethylamine → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide

HRID 2382146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382146
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=1.[CH3:17][O:18][C:19]1[N:24]=[C:23]2[C:25]([CH3:29])=[CH:26][N:27]([NH2:28])[C:22]2=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:17][O:18][C:19]1[N:24]=[C:23]2[C:25]([CH3:29])=[CH:26][N:27]([NH:28][C:14]([C:10]3[C:11]([CH3:13])=[N:12][C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:8][CH:9]=3)=[O:16])[C:22]2=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 685551495-Methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine

Produkt 1

HCID 592000424-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amideAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-pyridin-2-yl-4-methyl-pyrimidine-5-carboxylic acid (1.69 mmol), 5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine (1.69 mmol), DIPEA (5.01 mmol) and HATU (2.03 mmol) in anhydrous DMF (8 mL) is stirred at 90° C. for 16 h. DMF is evaporated in vacuo. The residue is dissolved in EtOAc (40 mL), and washed with water (3×10 mL) and brine (10 mL). The organic layer is dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 0-15% MeOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide (295 mg) as a solid. MS: 375 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.40 (s, 3H), 2.84 (s, 3H), 4.02 (s, 3H), 6.70 (d, H), 7.13 (s, H), 7.41 (m, H), 7.50 (d, H), 7.85 (t, H), 8.51 (m, 2H), 8.78 (s, 2H), 10.57 (br, N—H).

Aufarbeitung

  1. customDMF is evaporated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (40 mL)
  3. washwashed with water (3×10 mL) and brine (10 mL)
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with 0-15% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-27da5d693cb941f58902c728b9ea5b3e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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