Diisopropylethylamine → HCID 178488012, compound

HRID 1367970Notes

Reaction equation

HRID 1367970 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]([NH:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([C:23](O)=[O:24])[C:16]=3[N:15]=2)=[O:12])[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.Cl.[CH3:62][S:63]([C:66]1[CH:73]=[CH:72][C:69]([CH2:70][NH2:71])=[CH:68][CH:67]=1)(=[O:65])=[O:64]>CN(C=O)C.[Cl-].[Na+].O>[CH3:62][S:63]([C:66]1[CH:73]=[CH:72][C:69]([CH2:70][NH:71][C:23]([C:22]2[C:16]3[NH:15][C:14]([NH:13][C:11]([C:3]4[N:2]=[CH:1][C:10]5[C:5]([CH:4]=4)=[CH:6][CH:7]=[CH:8][CH:9]=5)=[O:12])=[N:18][C:17]=3[CH:19]=[CH:20][C:21]=2[O:26][CH3:27])=[O:24])=[CH:68][CH:67]=1)(=[O:64])=[O:65]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669407622-[(isoquinoline-3-carbonyl)-amino]-5-methoxy-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 178488012HCID 178488012, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

33 mg (0.1 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-5-methoxy-1H-benzoimidazole-4-carboxylic acid and 100 mg (0.25 mmol) of HBTU were dissolved in 1.0 mL of DMF and 0.4 mL of DIEA was treated with 32 mg (0.15 mmol) of 4-methanesulfonyl-benzylamine hydrochloride 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 25 mg (47%) of isoquinoline-3-carboxylic acid [7-(4-methanesulfonyl-benzylcarbamoyl)-6-methoxy-1H-benzoimidazol-2-yl]-amide. LCMS: 530 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-4bea3aca54084f6caf90d171b1a8b426
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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