Diisopropylethylamine → HCID 178522500, compound

HRID 1910228Notes

Reaction equation

HRID 1910228 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:31]([OH:33])=O)[C:12]2[NH:16][C:15]([NH:17]C(C3N=CC4C(C=3)=CC=CC=4)=O)=[N:14][C:13]=2[CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:60]([CH:64]([CH3:66])[CH3:65])[CH:61]([CH3:63])C.S(O)(O)(=O)=[O:68].[NH2:72][C:73]1[NH:74][CH:75]=[CH:76][N:77]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:31](=[O:33])[NH:72][C:73]2[NH:74][CH:75]=[CH:76][N:77]=2)[C:12]2[NH:16][C:15]([NH:17][C:66]([C:64]3[N:60]=[CH:61][C:63]4[C:45]([CH:65]=3)=[CH:46][CH:47]=[CH:48][CH:43]=4)=[O:68])=[N:14][C:13]=2[CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

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 178522501HCID 178522501, compound

Product 1

HCID 178522500HCID 178522500, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

300 mg (0.75 mmol) of 6-benzyloxy-2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carboxylic acid and 600 mg (1.58 mmol) of HBTU were dissolved in 2.0 mL of DMF and 1.0 mL of DIEA and reacted with 390 mg (3.0 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 300 mg (80%) of isoquinoline-3-carboxylic acid [5-benzyloxy-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 505 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-a74bfbf190354c29a76de082d94f4c03
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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