Imidazole → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12](O)=O)[S:11][C:7]=2[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[NH:21]1C=CN=C1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1.C(OC(=O)C)C>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]#[N:21])[S:11][C:7]=2[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:5][CH:4]=1Participants
Procedure
In accordance with scheme 6, to a solution of 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (for R1=morpholinyl, XII) and imidazole in pyridine was added at 0° C. phosphoroxychloride. After about 5 hours, the cold solution was diluted with ethylacetate and worked up in conventional manner to obtain 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile (IXX), which was dissolved in triethylamine and in pyridine and was then stirred for 4 hours with hydrogen sulfide at room temperature. Solvent and excess hydrogen sulfide were removed. The obtained 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amide (XX) was dissolved in tetrahydrofurane and was reacted with iodomethane at 50° C. for about 4 hours. All volatile components were distilled off under vacuum and the residue was dissolved in a solution of 4,4-diethoxy-tetrahydro-pyran-3-ylamine in tetrahydrofurane. The mixture was stirred at 50° C. overnight, the solvent was distilled off and the residue was suspended in hydrochloric acid and stirred for about 3 hours at room temperature. It was obtained (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-pyrano[3,4-d]imidazole Id1).
Sources & evidence
- ORD record
- ord-00709caceaa94b259bd7fc04cc0c97e3
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122545B2
Reaction notes
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