Dimethylformamide → Trifluoroacetic acid

HRID 58094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58094
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[N:16]3[N:17]=[C:18]([C:21](O)=[O:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:4]=1.F[B-](F)(F)F.[N:31]1([O:40][C:41](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl-].[NH4+].CCN(CC)CC.CN(C=[O:61])C>>[C:41]([OH:40])([C:2]([F:25])([F:24])[F:1])=[O:61].[F:25][C:2]([F:24])([F:1])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[N:16]3[N:17]=[C:18]([C:21]([NH2:31])=[O:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)[CH:4]=1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 897828553-(6-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid

Produkt 2

HCID 6422Trifluoroacetic acidHCID 897828523-(6-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-b]pyridazine-6-carboxamide

Versuchsvorschrift

To 3-(6-(trifluoromethyl)-1H-indazol-4-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid (0.036 g, 0.104 mmol) in DMF (3 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.028 g, 0.073 mmol), ammonium chloride (8.32 mg, 0.156 mmol), and Et3N (0.013 g, 0.124 mmol). The reaction mixture was stirred at room temperature overnight and was subsequently filtered and purified by preparative HPLC, eluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give a TFA salt of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.35-7.46 (m, 1H), 7.53 (t, J=7.58 Hz, 1H), 7.71 (d, J=8.59 Hz, 1H), 7.82 (dd, J=18.32, 9.47 Hz, 1H), 7.95-8.05 (m, 2H), 8.40 (t, J=9.35 Hz, 1H), 8.50 (br s, 1H), 8.57-8.66 (m, 1H), 8.70 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H9F3N6O, 347.1. found 347.2.

Aufarbeitung

  1. filtrationwas subsequently filtered
  2. custompurified by preparative HPLC
  3. washeluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-2b74a432e6084df582e038350dce3192
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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