Hydrochloric Acid → HCID 51039520, compound

HRID 17569Notes

Reaction equation

HRID 17569 reaction equation
[OH-].[Na+].[C:3]([C:5]1[C:10]2[N:11]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[O:13][C:9]=2[C:8]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:6]=1[CH3:37])#[N:4].Cl>C(O)C>[C:3]([C:5]1[C:10]2[N:11]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[O:13][C:9]=2[C:8]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:29])[CH3:30])[CH2:24]2)=[C:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:6]=1[CH3:37])#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 51041665Ethyl 4-({4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}amino)butanoate

Product 1

HCID 51039520HCID 51039520, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With cooling with ice, aqueous 1 N sodium hydroxide solution (536 μl, 0.536 mmol) was added to an ethanol (3.5 ml) solution of ethyl 4-({4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}amino)butanoate (I-281) (170 mg, 0.357 mmol), followed by stirring at room temperature for 15 hours. With cooling with ice, aqueous 1 N hydrochloric acid solution (536 μl, 0.536 mmol) was added to the reaction liquid, followed by concentration under reduced pressure. The resulting residue was purified by preparative TLC (eluent, chloroform:methanol=5:1, v/v) to obtain the entitled compound (110 mg, 69%) as a pale brown foamy substance.

Workup

  1. additionwas added to the reaction liquid
  2. concentrationfollowed by concentration under reduced pressure
  3. customThe resulting residue was purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record
ord-cb969adc4c4f4f4196361ad1ec100a6f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…