Methanesulfonic Acid → HCID 57785336, compound
Reaction equation
[CH:1]([NH:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:25][C:26]1[C:31]([Cl:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][C:27]=1[C:35](=[O:37])[CH3:36].CS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:35]([C:27]1[C:26]([NH:25][C:10]([C:8]2[N:9]=[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])[O:6][CH:7]=2)=[O:12])=[C:31]([Cl:32])[C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:37])[CH3:36]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2-isopropylaminooxazole-4-carboxylic acid (1.9 g, 10.9 mmol) in DCM (10 ml) was added CDI (1.8 g, 10.9 mmol). The mixture was then stirred at it for 2 h, followed by addition of 1-(2-Amino-3-chloro-4-methoxyphenyl)ethanone (prepared according to Raboisson, P. J.-M. B., et al., WO2007014926, p 78; 1.4 g, 8.7 mmol) and CH3SO3H (2.1 mL, 32.8 mmol), and then stirred for 18 h at rt. The reaction mixture was diluted with DCM (100 mL) and washed with 1N HCl (2×100 mL). To the collected DCM layer was added K2CO3 (3.02 g, 21.88 mmol) and stirred for 2 h at rt. The solution was filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel, eluting with EtOAc/hexane, to give 2-isopropylamino-oxazole-4-carboxylic acid (6-acetyl-2-chloro-3-methoxyphenyl)amide (863 mg, 22% yield). LCMS found 382 [M+H]+.
Workup
- stirringstirred for 18 h at rt
- washwashed with 1N HCl (2×100 mL)
- stirringstirred for 2 h at rt
- filtrationThe solution was filtered
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by flash chromatography on silica gel
- washeluting with EtOAc/hexane
Sources & evidence
- ORD record
- ord-f1a12984f9224377b466a1661ad99f02
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809267B2
Reaction notes
Loading…