Formaldehyde → Trifluoroacetic acid

HRID 2067897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067897
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24]([N:26]4[CH2:31][CH2:30][NH:29][CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])[CH:22]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[CH2:38]=[O:39].[O-:40]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[F:37][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24]([N:26]4[CH2:31][CH2:30][N:29]([CH3:38])[CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])[CH:22]=3)=[N:14][CH:15]=2)=[CH:8][CH:9]=1.[C:38]([OH:40])([C:32]([F:35])([F:34])[F:33])=[O:39]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 24436Sodium SulfateHCID 58542195N-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)piperazine-1-carboxamide

Produkt 2

HCID 6422Trifluoroacetic acidHCID 25196951N-(5-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)-4-methylpiperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)piperazine-1-carboxamide D11 (0.05 mmol), HCHO (0.15 mmol, 30% aqueous) and anhydrous Na2SO4 (1.5 mmol) in DCM (2 mL) is stirred at rt for 30 min. Then NaHB(OAc)3 (0.3 mmol) is added and the resulting mixture is stirred for 12 h. Purification by prep-HPLC (ACN gradient 10-70%) affords N-(5-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)-4-methylpiperazine-1-carboxamide D12 as a TFA salt. 1H NMR (400 MHz, d6-DMSO) δ 9.69 (s, 1H), 8.80 (s, 2H), 8.15 (s, 1H), 7.76 (d, J=8.8 Hz, 2H), 7.61 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.28 (t, J=74.0 Hz, 1H), 7.27 (d, J=8.8 Hz, 2H), 7.09 (d, J=8.4 Hz, 1H), 3.68 (m, 1H), 3.54 (m, 1H), 2.88 (m, 1H), 2.51 (m, 4H), 2.47 (s, 1H), 2.09 (s, 3H). MS (m/z) (M+1)+: 537.2.

Aufarbeitung

  1. customPurification by prep-HPLC (ACN gradient 10-70%)

Quellen und Nachweise

ORD-Eintrag
ord-fc40094233ae45858407ed95ec5028a5
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293757B2

Notizen zur Reaktion

Wird geladen…