Dimethyl Sulfoxide → [1-amino(4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]amino}phenyl)methylene]carbamic acid 2-methylallyl ester

HRID 2089689

Reaction equation

HRID 2089689 reaction equation
CO[C@H](C1C=CC=CC=1)C(O)=O.[F:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][OH:23])=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[C@@H:26]([NH:39][C:40]1[CH:48]=[CH:47][C:43]([C:44]([NH2:46])=[NH:45])=[CH:42][CH:41]=1)[C:27]1[NH:31][C:30](=[O:32])[N:29]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[N:28]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.C1([O:65][C:66](=O)[O:67][CH2:68][C:69]([CH3:71])=[CH2:70])C=CC=CC=1>C(O)(=O)C.O.C(OCC)(=O)C>[CH3:71][C:69](=[CH2:70])[CH2:68][O:67][C:66](=[O:65])[N:45]=[C:44]([C:43]1[CH:42]=[CH:41][C:40]([NH:39][C@H:26]([C:15]2[CH:16]=[C:17]([O:24][CH3:25])[CH:18]=[C:19]([O:20][CH2:21][CH2:22][OH:23])[C:14]=2[F:13])[C:27]2[NH:31][C:30](=[O:32])[N:29]([C:33]3[N:34]=[CH:35][CH:36]=[CH:37][N:38]=3)[N:28]=2)=[CH:48][CH:47]=1)[NH2:46]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 151790822-Methyl-allyl phenyl carbonateHCID 1363340344-{[(R)-[2-fluoro-3-(2-hy droxy ethoxy)-5-methoxyphenyl] (5-oxo-1-pyrimidi n-2-yl-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}benzamidine (R)-methoxyphenylacetate

Product 1

HCID 136334036[1-amino(4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]amino}phenyl)methylene]carbamic acid 2-methylallyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}benzamidine (R)-methoxyphenylacetate (0.5 g, 0.755 mmol), potassium carbonate (104 mg, 0.755 mmol), and dimethyl sulfoxide (1.5 mL), carbonic acid 2-methylallyl ester phenyl ester [CAS No. 138621-73-5] (145 mg, 0.755 mmol) was added, and the resulting mixture was stirred at 60° C. for 2 hours and 30 minutes. After cooling the mixture, the reaction solution was added to a mixture of ethyl acetate (5 mL) and water (15 mL), and an aqueous acetic acid solution (prepared from acetic acid (0.1 mL) and water (5 mL)) was added dropwise to the resulting mixture with stirring. The precipitated solid was filtered and sequentially washed with ethyl acetate (10 mL) and water (10 mL). The solid obtained was dried under air flow to obtain the captioned compound (361 mg) as a yellow solid.

Workup

  1. addition138621-73-5] (145 mg, 0.755 mmol) was added
  2. temperatureAfter cooling the mixture
  3. stirringwith stirring
  4. filtrationThe precipitated solid was filtered
  5. washsequentially washed with ethyl acetate (10 mL) and water (10 mL)
  6. customThe solid obtained
  7. customwas dried under air flow

Sources & evidence

ORD record
ord-4dc6f673ba6646939261371be185efe3
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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