Hydrochloric Acid → HCID 68584985, compound

HRID 17492Notes

Reaction equation

HRID 17492 reaction equation
[OH-].[Na+].[C:3]([C:5]1[C:10]2[N:11]=[C:12]([C:14]3[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=3)[O:13][C:9]=2[C:8]([N:24]2[CH2:28][CH2:27][C@H:26]([N:29]([CH3:31])[CH3:30])[CH2:25]2)=[C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:6]=1[CH3:38])#[N:4].Cl>C(O)C>[C:3]([C:5]1[C:10]2[N:11]=[C:12]([C:14]3[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=3)[O:13][C:9]=2[C:8]([N:24]2[CH2:28][CH2:27][C@H:26]([N:29]([CH3:31])[CH3:30])[CH2:25]2)=[C:7]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:6]=1[CH3:38])#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68585881Ethyl 2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-1,3-thiazole-4-carboxylate

Product 1

HCID 68584985HCID 68584985, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

Aqueous 1 N sodium hydroxide solution (225 μl, 0.225 mmol) was added to an ethanol (1.7 ml) solution of ethyl 2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-1,3-thiazole-4-carboxylate (I-198) (87.0 mg, 0.173 mmol), followed by stirring in an oil bath at 45° C. for 1 hour. With cooling with ice, 1 N hydrochloric acid (225 μl, 0.225 mmol) was added to the reaction liquid, followed by concentration, under reduced pressure, and the obtained pale yellow solid was purified in slurry with a mixed solvent of ethanol:water=9:1 to obtain the entitled compound (50.0 mg, 59.7%) as a pale yellow solid.

Workup

  1. additionwas added to the reaction liquid
  2. concentrationfollowed by concentration, under reduced pressure
  3. customthe obtained pale yellow solid was purified in slurry with a mixed solvent of ethanol

Sources & evidence

ORD record
ord-7d4e656cad8b48d4b902b266165085fe
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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