1,2-Dichloroethane → 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide

HRID 1802056

Reaktionsgleichung

Reaktionsgleichung von HRID 1802056
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[CH3:18])[C:5]([C:19]([OH:21])=O)=[CH:4][N:3]=1.[CH:22]1[CH:23]=[CH:24][C:25]2[N:30]([OH:31])[N:29]=[N:28][C:26]=2[CH:27]=1.C(Cl)CCl.[NH3:36]>CN(C=O)C.CCOC(C)=O.O>[N:30]1([O:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH:11]=[CH:12][N:13]4[CH3:18])[C:5]([C:19]([NH2:36])=[O:21])=[CH:4][N:3]=2)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:27][C:26]=2[N:28]=[N:29]1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 574720122-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid

Produkt 1

HCID 574720132-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamideAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid (325 mg, 1.08 mmol) and HOBt (198 mg, 1.29 mmol) in DMF (4 mL), EDC (248 mg, 1.29 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 8.00 mL, and 4.00 mmol) was added. It was stirred at room temperature overnight. Water and EtOAc were added. The organic phase was separated, washed with 1 N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide (378 mg). MS 401.4 (M+H)

Aufarbeitung

  1. stirringIt was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 1 N HCl
  4. dry with materialwith 5% NaHCO3, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-742b04e1009644309b510c14c1dac161
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349860B2

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