4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide

HRID 2382071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382071
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[N:3]=1.[CH2:16]([C:18]1[C:22]2=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=[C:21]2[N:20]([NH2:31])[CH:19]=1)[CH3:17].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH2:16]([C:18]1[C:22]2=[N:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=[C:21]2[N:20]([NH:31][C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[N:5][CH:6]=2)=[O:10])[CH:19]=1)[CH3:17]

Komponenten

6

Edukt 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 685536304-methyl-2-(2-thiazolyl)-5-Pyrimidinecarboxylic acidHCID 685552233-Ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-ylamine

Produkt 1

HCID 591999754-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amideAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (88 mg, 0.40 mmol) and 3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-ylamine (89 mg, 0.40 mmol) in DMF (5 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (113 mg, 0.41 mmol) and stirred at 50° C. overnight. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and stirred for 10 min. The precipitate is collected by filtration, washed with H2O (50 mL) and heptane (50 mL), and dried in vacuo to afford 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide (75 mg, 40%). MS: 433 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 12.19 (s, NH, 1H), 9.28 (s, 1H), 8.15 (m, 2H), 8.08 (d, 1H), 7.87 (s, 1H), 7.72 (d, 1H), 2.83 (q, 2H), 2.77 (s, 3H), 1.35 (t, 3H).

Aufarbeitung

  1. stirringstirred for 10 min
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with H2O (50 mL) and heptane (50 mL)
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-05d19c887b8f481192b643b8042e5a1b
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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