Benzenepropanoic acid → HCID 178520434, compound

HRID 1910199Notes

Reaction equation

HRID 1910199 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:36][C:37]1[CH:38]=[C:39]([C:59](=[O:66])[NH:60][C:61]2[NH:62][CH:63]=[CH:64][N:65]=2)[C:40]2[N:44]=[C:43]([NH:45][C:46]([C:48]3[N:49]=[CH:50][C:51]4[C:56]([CH:57]=3)=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:47])[NH:42][C:41]=2[CH:58]=1>CN(C=O)C.CCN(C(C)C)C(C)C.[Cl-].[Na+].O>[NH:62]1[CH:63]=[CH:64][N:65]=[C:61]1[NH:60][C:59]([C:39]1[C:40]2[NH:44][C:43]([NH:45][C:46]([C:48]3[N:49]=[CH:50][C:51]4[C:56]([CH:57]=3)=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:47])=[N:42][C:41]=2[CH:58]=[C:37]([NH:36][C:9](=[O:11])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:38]=1)=[O:66]

Participants

7

Reactant 3

HCID 107Benzenepropanoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58724420HCID 58724420, compound

Product 1

HCID 178520434HCID 178520434, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

60 mg (0.4 mmol) of 3-phenyl-propionic acid and 170 mg (0.45 mmol) of HBTU in a mixture of 1.0 mL of DMF and 0.5 mL of DIEA was reacted with 120 mg (0.3 mmol) of the isoquinoline-3-carboxylic acid [6-amino-4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide (See Example 130) as described in general procedure A. After the reaction was complete, it was diluted with brine (20 mL). The resulting solid was filtered, washed with water, ethyl acetate and dried under vacuum to give 101 mg (66%) of isoquinoline-3-carboxylic acid [7-(1H-imidazol-2-ylcarbamoyl)-5-(3-phenyl-propionylamino)-1H-benzoimidazol-2-yl]-amide as a solid. LCMS: 545 (M+1)+.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water, ethyl acetate
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b99b9e8531554a39b30e86ee38e8de59
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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