1,1'-Carbonyldiimidazole → HCID 86595000, compound
Reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]([OH:12])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][C:28]=1[NH2:39]>>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)=[CH:29][C:28]=1[NH:39][C:10]([C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[O:12]Participants
Procedure
In accordance with scheme 3, to a suspension of a corresponding benzoimidazole-2-carboxylic acid (XIII) was added CDI and stirred at ambient temperature for about 1 h. Then the mixture is refluxed for about 30 min. After cooling to ambient temperature, 2-methoxy-5-morpholin-4-yl-phenylamine (for R1=morpholinyl, IX) was added and the reaction mixture was heated to reflux for about 16 h. After workup, the corresponding 1H-benzoimidazole-2-carboxylic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (XIV) was obtained, which was then taken up in toluene and treated with Lawesson reagent. The reaction mixture was heated to reflux for about 2 h and after workup, the corresponding 1H-benzoimidazole-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (IV) was obtained, which was then taken up in water and treated with KOH and potassium hexacyano ferrate at reflux for about 24 h to obtain the corresponding 2-(1H-benzoimidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole (Ib).
Workup
- temperatureThen the mixture is refluxed for about 30 min
- temperatureAfter cooling to ambient temperature
- temperaturethe reaction mixture was heated
- temperatureto reflux for about 16 h
Sources & evidence
- ORD record
- ord-1cd54603abc04058a19d58ad70dd8022
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122545B2
Reaction notes
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