Diisopropylethylamine → HCID 58724446, compound

HRID 1367985Notes

Reaction equation

HRID 1367985 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-15c49216a93c46c2a2c45b1318d33b86
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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