Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

HRID 1363239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363239
C([N:5]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[NH:16][C:17]1[N:22]=[C:21]([S:23][C:24]#[N:25])[C:20]([N+:26]([O-:28])=[O:27])=[CH:19][N:18]=1)C(=O)O)(C)(C)C.FC1C=CC2N=CN(C3N=C(SC#N)C([N+]([O-])=O)=CN=3)C=2C=1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52].C(Cl)Cl>>[F:15][C:12]1[CH:11]=[C:10]([NH:16][C:17]2[N:22]=[C:21]([S:23][C:24]#[N:25])[C:20]([N+:26]([O-:28])=[O:27])=[CH:19][N:18]=2)[C:9]([NH2:5])=[CH:14][CH:13]=1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]

Komponenten

4

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 866248536-Fluoro-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate

Produkt 2

HCID 6422Trifluoroacetic acidHCID 598463355-fluoro-N1-(5-nitro-4-thiocyanatopyrimidin-2-yl)benzene-1,2-diamine

Versuchsvorschrift

6-Fluoro-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate (4.06 g) was dissolved in 30% TFA/DCM (50 mL) and stirred until no starting material remained (90 min). The reaction solvents were removed, to yield crude 5-fluoro-N1-(5-nitro-4-thiocyanatopyrimidin-2-yl)benzene-1,2-diamine (MH+=306) as a TFA salt that was used immediately as such in the next step. Trimethyl ortho formate (15 mL) and MeOH (100 mL) were added to the above diamine and the solution was stirred for 16 hrs. The resulting orange ppt was collected via filtration, washed with MeOH and dried under reduced pressure to yield the titled compound (2.62 g), 1H-NMR (400 MHz, d6-DMSO) δ 9.2 (s, 1H), 9.1 (s, 1H), 8.5 (dd, 1H), 7.8 (dd, 1H), 7.3 (dd, 1H) ppm; MH+=317.

Aufarbeitung

  1. custom(90 min)
  2. customThe reaction solvents were removed

Quellen und Nachweise

ORD-Eintrag
ord-2923a22a61b34b0e9c56fa9a56704059
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884109B2

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