Dimethyl Sulfoxide → Trifluoroacetic acid

HRID 12415Notes

Reaction equation

HRID 12415 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)C=CC=CC=1.Cl.[F:29][C:30]1[CH:31]=[C:32]([CH:38]=[C:39]([F:41])[CH:40]=1)[O:33][CH2:34][CH:35]([NH2:37])[CH3:36].CS(C)=[O:44].C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[F:23][C:22]([F:25])([F:24])[C:21]([OH:26])=[O:33].[OH:44][C:21]([C:22]([F:25])([F:24])[F:23])=[O:26].[F:29][C:30]1[CH:31]=[C:32]([CH:38]=[C:39]([F:41])[CH:40]=1)[O:33][CH2:34][CH:35]([NH:37][C:8]([NH:9][C:10]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[CH:15]2)=[O:27])[CH3:36]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 231340121-(3,5-Difluorophenoxy)propan-2-amine hydrochlorideHCID 860430848-(Trifluoroacetylamino)isoquinolin-5-ylcarbamic acid phenyl ester

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 86609358HCID 86609358, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 8-(trifluoroacetylamino)isoquinolin-5-ylcarbamic acid phenyl ester (35 mg) were added 2-(3,5-difluorophenoxy)-1-methylethylamine hydrochloride (22 mg) obtained in Example 52 as a synthetic intermediate, dimethyl sulfoxide (1 ml) and N,N-diisopropylethylamine (81 μl), and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate and, after washing with water, the solvent was evaporated. The obtained crude product was purified by reversed-phase high performance liquid chromatography (reversed-phase HPLC) (water-acetonitrile, each containing 0.1% trifluoroacetic acid (TFA)) to give N-[2-(3,5-difluorophenoxy)-1-methylethyl]-N′-[8-(trifluoroacetylamino)isoquinolin-5-yl]urea TFA salt (13.7 mg).

Workup

  1. washafter washing with water
  2. customthe solvent was evaporated
  3. customThe obtained crude product
  4. customwas purified by reversed-phase high performance liquid chromatography (reversed-phase HPLC) (water-acetonitrile

Sources & evidence

ORD record
ord-8e334d07d49a400c969557c248621aab
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Reaction notes

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