Triethylamine → HCID 178508420, Verbindung

HRID 2173705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173705
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=O)=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.CCN(CC)CC.[F:23][C:24]([F:32])([F:31])[C:25]1[CH:29]=[C:28]([NH2:30])[NH:27][N:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[F:23][C:24]([F:32])([F:31])[C:25]1[CH:29]=[C:28]([NH:30][C:13]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([C:8]([F:9])([F:10])[F:11])=[C:5]([Br:12])[N:4]=2)=[O:15])[NH:27][N:26]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584422963-Amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid2×HCID 178507669HCID 178507669, Verbindung

Produkt 1

HCID 178508420HCID 178508420, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (100 mg, 0.350 mmol) in dry NMP (2 ml) was added NEt3 (0.097 ml, 0.699 mmol) followed by 3-(trifluoromethyl)-1H-pyrazol-5-amine (48.0 mg, 0.318 mmol). The mixture was stirred at RT for 5 minutes, before treating with HATU (133 mg, 0.350 mmol). The resulting orange solution was stirred at RT for 10 minutes and then partitioned between EtOAc (50 ml) and 1M NaOH (30 ml). The organic portion was separated and washed with 1M NaOH (20 ml), water (20 ml), dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc) afforded the title compound as a yellow solid.

Aufarbeitung

  1. stirringThe resulting orange solution was stirred at RT for 10 minutes
  2. custompartitioned between EtOAc (50 ml) and 1M NaOH (30 ml)
  3. customThe organic portion was separated
  4. washwashed with 1M NaOH (20 ml), water (20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude residue by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-286af4ac62094de495c699db7d9039e1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056867B2

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