Methanesulfonic Acid → 3-methoxy-2,2-dimethylpropionic acid 5-[(R)-[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]-triazol-3-yloxymethyl ester methanesulfonate

HRID 2089669Notes

Reaction equation

HRID 2089669 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([F:56])=[C:10]([C@@H:16]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([NH2:55])=[N:47][C:48]([O:50][CH2:51][C:52]([CH3:54])=[CH2:53])=[O:49])=[CH:42][CH:41]=2)[C:17]2[N:18]=[C:19]([O:28][CH2:29][O:30][C:31](=[O:38])[C:32]([CH3:37])([CH3:36])[CH2:33][O:34][CH3:35])[N:20]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:21]=2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)(=[O:3])[CH3:2].[CH3:57][S:58]([OH:61])(=[O:60])=[O:59]>C(OCC)(=O)C>[CH3:57][S:58]([OH:61])(=[O:60])=[O:59].[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([F:56])=[C:10]([C@@H:16]([NH:39][C:40]2[CH:41]=[CH:42][C:43]([C:46]([NH2:55])=[N:47][C:48]([O:50][CH2:51][C:52]([CH3:54])=[CH2:53])=[O:49])=[CH:44][CH:45]=2)[C:17]2[N:18]=[C:19]([O:28][CH2:29][O:30][C:31](=[O:38])[C:32]([CH3:37])([CH3:36])[CH2:33][O:34][CH3:35])[N:20]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:21]=2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 674711843-methoxy-2,2-dimethylpropionic acid 5-[(R)-[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

Product 1

HCID 866774013-methoxy-2,2-dimethylpropionic acid 5-[(R)-[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]-triazol-3-yloxymethyl ester methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

At room temperature, 3-methoxy-2,2-dimethylpropionic acid 5-[(R)-[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester (Example 6f, 50 mg) was dissolved in ethyl acetate (5 mL), and a solution of methanesulfonic acid (0.0041 mL) in ethyl acetate (0.5 mL) was added dropwise thereto. The resulting mixture was stirred overnight at room temperature, and the precipitated solid was filtered. The filtrate obtained was washed with ethyl acetate and TBME, and dried. The captioned compound (48 mg) was obtained.

Workup

  1. filtrationthe precipitated solid was filtered
  2. customThe filtrate obtained
  3. washwas washed with ethyl acetate and TBME
  4. customdried

Sources & evidence

ORD record
ord-55d1ba8773034d909b491aaca936c356
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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