Formic Acid → 2-(2-(4-(2-(Methylamino)ethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162787

Reaktionsgleichung

Reaktionsgleichung von HRID 1162787
CS(O[CH2:6][CH2:7][C:8]1[C:9]([C:29]([F:32])([F:31])[F:30])=[N:10][N:11]([CH2:13][C:14]([NH:16][C:17]2[S:21][C:20]3[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=3[C:18]=2[C:26](=[O:28])[NH2:27])=[O:15])[CH:12]=1)(=O)=O.[CH3:33][NH2:34].C(O)=O>CN(C=O)C>[CH3:33][NH:34][CH2:6][CH2:7][C:8]1[C:9]([C:29]([F:30])([F:32])[F:31])=[N:10][N:11]([CH2:13][C:14]([NH:16][C:17]2[S:21][C:20]3[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=3[C:18]=2[C:26]([NH2:27])=[O:28])=[O:15])[CH:12]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 6329MethylamineHCID 595204612-(1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)1H-pyrazol-4-yl)ethyl methanesulfonate

Produkt 1

HCID 595204662-(2-(4-(2-(Methylamino)ethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The 2-(1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)1H-pyrazol-4-yl)ethyl methanesulfonate (30 mg, 0.061 mmol) was dissolved in DMF (1 mL) and methylamine (2 M in THF, 1 mL, 2 mmol) added. The reaction mixture was heated at 120° C. for 5 min in the microwave. The THF was removed in vacuo and the reaction mixture filtered and purified by preparative reverse phase HPLC to give the formic acid salt of the desired product (3.6 mg, 0.008 mmol, 12%).

Aufarbeitung

  1. customThe THF was removed in vacuo
  2. filtrationthe reaction mixture filtered
  3. custompurified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4fcfae59353649e49cdea4ee85fd3982
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820707B2

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