Reaction equation
[CH2:1]([S:3][C:4]1[CH:5]=[C:6]([C:26]([OH:28])=O)[C:7]2[NH:11][C:10]([NH:12][C:13]([C:15]3[N:16]=[CH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:14])=[N:9][C:8]=2[CH:25]=1)[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.S(O)(O)(=O)=O.[NH2:67][C:68]1[NH:69][CH:70]=[CH:71][N:72]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:1]([S:3][C:4]1[CH:5]=[C:6]([C:26](=[O:28])[NH:67][C:68]2[NH:69][CH:70]=[CH:71][N:72]=2)[C:7]2[NH:11][C:10]([NH:12][C:13]([C:15]3[N:16]=[CH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:14])=[N:9][C:8]=2[CH:25]=1)[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
80 mg (0.2 mmol) of 6-ethylsulfanyl-2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carboxylic acid and 300 mg (0.76 mmol) of HBTU were dissolved in 1.0 mL of DMF and 0.5 mL of DIEA and treated with 132 mg (1.0 mmol) of 2-aminoimidazole sulfate as described in general procedure A. Upon completion, the reaction was diluted with brine. The resulting solid was filtered, washed with water and EtOAc, and dried under vacuum to produce 66 mg (71%) of isoquinoline-3-carboxylic acid [5-ethylsulfanyl-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 458 (M+1)+.
Workup
- filtrationThe resulting solid was filtered
- washwashed with water and EtOAc
- customdried under vacuum
Sources & evidence
- ORD record
- ord-12b35ee786794bb4b2d51cf1b2c37cb7
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946259B2
Linked notes
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