Trifluoroacetic acid methylene chloride → Trifluoroacetic acid
Reaction equation
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]Participants
Reactant 2
Product 2
Procedure
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.
Workup
- custom(90 min)
- customThe reaction solvents were removed
Sources & evidence
- ORD record
- ord-2923a22a61b34b0e9c56fa9a56704059
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884109B2
Reaction notes
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