Water → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine
Reaction equation
CO[C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.Br[C:13]1[N:18]=[CH:17][C:16](N)=[CH:15][CH:14]=1.CO[C:22]1N=CC(C2SC3C=CC=CC=3N=2)=C[N:23]=1.O.CCO[C:41](C)=[O:42]>>[CH3:41][O:42][C:11]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:16]3[CH:15]=[CH:14][C:13]([NH:23][CH3:22])=[N:18][CH:17]=3)=[N:7][C:6]=2[CH:10]=1Participants
Conditions
- Temperature
- 170 °C
Procedure
6-Methoxy-1,3-benzothiazole (60 mg, 0.36 mmol) and 6-bromopyridin-3-amine (76 mg, 0.44 mmol) were reacted according to the procedure used for the preparation of 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole with the exception that the reaction was heated at 170° C. in a microwave reactor for 1.5 h. Water and EtOAc were added and the mixture was filtered. The phases of the filtrate were separated and the aqueous layer was extracted with EtOAc (3×). The organic phase was washed with brine, dried (MgSO4) and concentrated under vacuum. Purification by flash chromatography (Heptan/EtOAc) followed by preparative HPLC gave the title compound (22 mg) as an off-white solid. 1H NMR (CHLOROFORM-d) δ 8.16-8.11 (m, 2H) 7.91 (d, 1H) 7.38 (d, 1H) 7.11-7.05 (m, 2H) 4.01 (br s, 2H) 3.91 (s, 3H); MS m/z (M+H) 258.
Workup
- filtrationthe mixture was filtered
- customThe phases of the filtrate were separated
- extractionthe aqueous layer was extracted with EtOAc (3×)
- washThe organic phase was washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated under vacuum
- customPurification by flash chromatography (Heptan/EtOAc)
Sources & evidence
- ORD record
- ord-78bb4d6c985f4539b80499cc3a37cd27
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163928B2
Reaction notes
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