4-Methylmorpholine → 4-amino-5-(4-amino-3-fluorophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

HRID 2197526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197526
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=3)[C:9]([C:11]([OH:13])=O)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:22][C:23]([F:27])([F:26])[CH2:24][NH2:25].N1C2C=CC=C(O[P+](N(C)C)(N(C)C)N(C)C)C=2N=N1.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=3)[C:9]([C:11]([NH:25][CH2:24][C:23]([F:27])([F:26])[F:22])=[O:13])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 595491934-Amino-5-(4-amino-3-fluorophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acidHCID 178486078HCID 178486078, Verbindung

Produkt 1

HCID 595491724-amino-5-(4-amino-3-fluorophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-amino-5-(4-amino-3-fluorophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (24.6 g, 85.6 mmol) was added to a mixture of 2,2,2-trifluoro-1-aminoethane (42.4 g, 428 mmol), benzotriazolyloxytris(dimethylamino)phosphonium PF6 (56.8 g, 128 mmol) and 4-methylmorpholine (43.3 g, 428 mmol) in DMF (500 mL). The reaction mixture was stirred at rt for 16 h. The resulting precipitate was isolated by filtration and then washed with acetone and diethyl ether to give the desired product (22 g, 70%); 1H NMR (300 MHz, DMSO-d6) δ 8.37 (dd, J=8.5, 8.5 Hz, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.92-8.03 (br s, 1H), 7.89 (s, 1H), 6.99 (dd, J=12.2, 1.8 Hz, 1H), 6.85 (dd, J=12.2, 1.8 Hz, 1H), 6.74-6.6.82 (m, 1H), 5.35 (s, 2H), 5.13-3.22 (br s, 1H), 3.87-4.01 (m, 2H); ES-MS m/z 369.2 (MH)+; HPLC RT (Method B) 2.05 min.

Aufarbeitung

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with acetone and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5de83a4b89f8431c95ae6420c32dfb2e
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338594B2

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