Diisopropylethylamine → 6,7-dimethoxy-isoquinoline-3-carboxylic acid [5-ethoxy-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide

HRID 1910244

Reaction equation

HRID 1910244 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][C:7]([C:15]([NH:17][C:18]1[NH:22][C:21]3[CH:23]=[C:24]([O:30][CH2:31][CH3:32])[CH:25]=[C:26]([C:27]([OH:29])=O)[C:20]=3[N:19]=1)=[O:16])=[CH:6]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.[NH2:71][C:72]1[NH:73][CH:74]=[CH:75][N:76]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:31]([O:30][C:24]1[CH:25]=[C:26]([C:27](=[O:29])[NH:71][C:72]2[NH:73][CH:74]=[CH:75][N:76]=2)[C:20]2[NH:19][C:18]([NH:17][C:15]([C:7]3[N:8]=[CH:9][C:10]4[C:5]([CH:6]=3)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=4)=[O:16])=[N:22][C:21]=2[CH:23]=1)[CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669408302-[(6,7-dimethoxy-isoquinoline-3-carbonyl)-amino]-6-ethoxy-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 1784668156,7-dimethoxy-isoquinoline-3-carboxylic acid [5-ethoxy-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amideYield 47.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

100 mg (0.25 mmol) of 2-[(6,7-dimethoxy-isoquinoline-3-carbonyl)-amino]-6-ethoxy-1H-benzoimidazole-4-carboxylic acid and 200 mg (0.53 mmol) of HBTU were dissolved in 1.0 mL of DMF and 0.5 mL of DIEA and treated with 200 mg (1.5 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 60 mg (47%) of 6,7-dimethoxy-isoquinoline-3-carboxylic acid [5-ethoxy-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 502 (M+1)+.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water and EtOAc
  3. customdried under vacuum

Sources & evidence

ORD record
ord-873ab1accd894e268e6a6c2def3fe919
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Linked notes

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