Hydrochloric Acid → HCID 136052978, compound

HRID 1916279Notes

Reaction equation

HRID 1916279 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:22](=[O:24])[NH:21][C:20]([CH3:25])=[N:19][C:18]=3[N:17]=[C:16]([S:26][CH2:27][C:28]3[N:29]=[C:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[O:31][CH:32]=3)[C:15]=2[C:40]#[N:41])=[CH:10][CH:9]=1)(=O)C.[OH-].[Li+].Cl>O1CCOCC1.O.O>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C:30]2[O:31][CH:32]=[C:28]([CH2:27][S:26][C:16]3[C:15]([C:40]#[N:41])=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][OH:4])=[CH:9][CH:10]=4)[C:23]4[C:22](=[O:24])[NH:21][C:20]([CH3:25])=[N:19][C:18]=4[N:17]=3)[N:29]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 136052980HCID 136052980, compound

Product 1

HCID 136052978HCID 136052978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

95 mg (0.162 mmol) of 2-{4-[7-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-6-cyano-2-methyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-5-yl]phenoxy}ethyl acetate were initially charged in 10 ml of a dioxane/water mixture 2:1, 7.7 mg (0.323 mmol) of lithium hydroxide were added and the mixture was stirred at RT for 5 h. The reaction mixture was then diluted with water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. The residue was purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5, with 0.1% TFA added). This gave 88 mg (99% of theory) of the target compound.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record
ord-657be9311f254c579643dfc80aafc1f9
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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