Isoquinoline-3-carboxylic acid → HCID 178507451, compound

HRID 1910134Notes

Reaction equation

HRID 1910134 reaction equation
[N+:1]([C:4]1[C:9]2[NH:10][C:11]([NH2:13])=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]([C:24](O)=[O:25])[N:15]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].O>[NH2:1][C:4]1[C:9]2[NH:10][C:11]([NH:13][C:24]([C:16]3[N:15]=[CH:14][C:23]4[C:18]([CH:17]=3)=[CH:19][CH:20]=[CH:21][CH:22]=4)=[O:25])=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 124656Isoquinoline-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508184HCID 178508184, compound

Product 1

HCID 178507451HCID 178507451, compoundYield 41.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1.42 g (8 mmol) of above 7-nitro-1H-benzoimidazol-2-ylamine was reacted with 1.38 g (8 mmol) of isoquinoline-3-carboxylic acid, 3.4 g (9 mmol) of HBTU in 30.0 mL of DMF and 5.0 mL of DIEA as described in general procedure A. After cooling to room temperature, the reaction mixture was diluted with 60 mL of saturated NaHCO3 and 100 mL of water. The solid was collected by filtration and washed with water and dried under reduced pressure, and subsequently subjected to hydrogenation as described in general procedure C to give 1.0 g (41%) of the isoquinoline-3-carboxylic acid (7-amino-1H-benzoimidazol-2-yl)-amide. LCMS: 304 (M+1)+

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-555a307f5e0e40d5a5ecee326dc29009
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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