Diisopropylethylamine → HCID 178498965, compound

HRID 1910239Notes

Reaction equation

HRID 1910239 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[N:2]=1.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.[CH3:47][O:48][C:49]([C:51]1[C:59]2[N:58]=[C:57]([NH2:60])[NH:56][C:55]=2[CH:54]=[CH:53][C:52]=1[O:61][CH3:62])=[O:50]>CN(C=O)C.[Cl-].[Na+].O>[CH3:47][O:48][C:49]([C:51]1[C:59]2[NH:58][C:57]([NH:60][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:13])=[N:56][C:55]=2[CH:54]=[CH:53][C:52]=1[O:61][CH3:62])=[O:50]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 124656Isoquinoline-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66940817HCID 66940817, compound

Product 1

HCID 178498965HCID 178498965, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

400 mg (2.0 mmol) of isoquinoline-3-carboxylic acid and 800 mg (2.1 mmol) of HBTU were dissolved in 2.0 mL of DMF and 1.3 mL of DIEA and treated with 300 mg (1.5 mmol) of 2-amino-5-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester 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 160 mg (28%) of 2-[(isoquinoline-3-carbonyl)-amino]-5-methoxy-3H-benzoimidazole-4-carboxylic acid methyl ester. LCMS: 377 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-e6b93957dd0648758eb3ca7aae129f43
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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