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

HRID 1910240Notes

Reaction equation

HRID 1910240 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([C:23]([OH:25])=O)[C:16]=3[N:15]=2)=[O:12])[N:2]=1.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.[NH2:66][C:67]1[NH:68][CH:69]=[CH:70][N:71]=1>CN(C=O)C.[Cl-].[Na+].O>[NH:68]1[CH:69]=[CH:70][N:71]=[C:67]1[NH:66][C:23]([C:22]1[C:16]2[NH:15][C:14]([NH:13][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:12])=[N:18][C:17]=2[CH:19]=[CH:20][C:21]=1[O:26][CH3:27])=[O:25]

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 669407622-[(isoquinoline-3-carbonyl)-amino]-5-methoxy-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 178488011isoquinoline-3-carboxylic acid [7-(1H-imidazol-2-ylcarbamoyl)-6-methoxy-1H-benzoimidazol-2-yl]-amideYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

66 mg (0.18 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-5-methoxy-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 was 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 26 mg (34%) of isoquinoline-3-carboxylic acid [7-(1H-imidazol-2-ylcarbamoyl)-6-methoxy-1H-benzoimidazol-2-yl]-amide. LCMS: 428 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-e3c4f8518e2f4e46bc125e26b138673d
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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