Diisopropylethylamine → HCID 58724446, compound

HRID 1910256Notes

Reaction equation

HRID 1910256 reaction equation
[F:1][C:2]1[C:23]([O:24][CH3:25])=[C:22]([F:26])[C:5]2[N:6]=[C:7]([NH:9][C:10]([C:12]3[N:13]=[CH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[O:11])[NH:8][C:4]=2[C:3]=1[C:27](O)=[O:28].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.[NH2:68][C:69]1[NH:70][CH:71]=[CH:72][N:73]=1>CN(C=O)C.[Cl-].[Na+].O>[F:26][C:22]1[C:5]2[N:6]=[C:7]([NH:9][C:10]([C:12]3[N:13]=[CH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[O:11])[NH:8][C:4]=2[C:3]([C:27](=[O:28])[NH:68][C:69]2[NH:70][CH:71]=[CH:72][N:73]=2)=[C:2]([F:1])[C:23]=1[O:24][CH3:25]

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 66940525HCID 66940525, compound

Product 1

HCID 58724446HCID 58724446, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

60 mg (0.15 mmol) of the above 5,7-difluoro-2-[(isoquinoline-3-carbonyl)-amino]-6-methoxy-3H-benzoimidazole-4-carboxylic acid and 100 mg (0.25 mmol) of HBTU were dissolved in 1.0 mL of DMF and 0.5 mL of DIEA and treated with 68 mg (0.5 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 24 mg (35%) of isoquinoline-3-carboxylic acid [4,6-difluoro-7-(1H-imidazol-2-ylcarbamoyl)-5-methoxy-1H-benzoimidazol-2-yl]-amide. LCMS: 464 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-92714fd3848a4ce59af97a7236440580
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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