Water → 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-(3-fluoro-4-imidazol-1-ylanilino)pyrimidine-5-carboxamide
Reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=O)OC(C)(C)C.N1(OC2[N:31]=[C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([N:39]4[CH:43]=[CH:42][N:41]=[CH:40]4)=[C:35]([F:44])[CH:34]=3)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=2)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1.CCOC(C)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH:43]=[CH:42][N:41]=[CH:40]3)=[C:35]([F:44])[CH:34]=2)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.30 M in NMP, 1.00 mL, 0.300 mmol) in NMP (1 mL) was added to 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide (57 mg, 0.13 mmol). DIEA (0.100 mL, 0.57 mmol) was also added. The mixture was stirred at 90 C for 1 h. After being cooled to room temperature, water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was dissolved in CH2Cl2 (1 mL) and TFA (1 mL). The solution was stirred at room temperature for 60 min. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (23 mg). MS 411.3 (M+H). UV λ=247.8, 299.8 nm.
Workup
- customThe organic phase was separated
- washwashed with 5% NaHCO3
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in CH2Cl2 (1 mL)
- stirringThe solution was stirred at room temperature for 60 min
- concentrationIt was concentrated in vacuo
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-ec2f9d848fbc4860b5eb8421da69f6db
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349860B2
Reaction notes
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