Diisopropylethylamine → HCID 178491597, compound

HRID 1910234Notes

Reaction equation

HRID 1910234 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[C:19]([O:26][CH3:27])=[CH:20][CH:21]=[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[C:19]([O:26][CH3:27])=[CH:20][CH:21]=2)=[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 66940349HCID 66940349, compound

Product 1

HCID 178491597HCID 178491597, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

33 mg (0.1 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-7-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 and reacted 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 14 mg (26%) of isoquinoline-3-carboxylic acid [7-(4-methanesulfonyl-benzylcarbamoyl)-4-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-c4147dfac3134a319437174974065b64
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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