Triethylamine → 5-[(1H-Indazol-4-ylmethyl)-carbamoyl]-3-isopropyl-thiophene-2-carboxylic acid methyl ester

HRID 1952620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952620
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13]([OH:15])=O)=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH:57]1[C:65]2[C:60](=[C:61]([CH2:66][NH2:67])[CH:62]=[CH:63][CH:64]=2)[CH:59]=[N:58]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:15])[NH:67][CH2:66][C:61]2[CH:62]=[CH:63][CH:64]=[C:65]3[C:60]=2[CH:59]=[N:58][NH:57]3)=[CH:8][C:9]=1[CH:10]([CH3:11])[CH3:12])=[O:4]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441192771-(1H-Indazol-4-yl)methanamineHCID 682270964-Isopropyl-5-(methoxycarbonyl)thiophene-2-carboxylic acid

Produkt 1

HCID 682267955-[(1H-Indazol-4-ylmethyl)-carbamoyl]-3-isopropyl-thiophene-2-carboxylic acid methyl esterAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-Isopropyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (190 mg, 0.83 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.35 mL, 2.49 mmol), HBTU (0.38 g, 1.0 mmol), HOBT (0.14 mg, 1.0 mmol), and C-(1H-Indazol-4-yl)-methylamine (180 mg, 1.25 mmol). The mixture was stirred at room temperature 15 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 30-100% EtOAc in hexane to afford the desired product (0.1262 g, 42% yield).

Aufarbeitung

  1. customquenched
  2. additionby pouring into EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with 30-100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-eba2ba67c1264f458a8e6c97a1e56c8c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404859B2

Notizen zur Reaktion

Wird geladen…