Lithium Hydroxide → HCID 136052976, compound

HRID 1916280Notes

Reaction equation

HRID 1916280 reaction equation
C([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:23](=[O:25])[NH:22][C:21]([CH2:26][CH3:27])=[N:20][C:19]=3[N:18]=[C:17]([S:28][CH2:29][C:30]3[N:31]=[C:32]([C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)[S:33][CH:34]=3)[C:16]=2[C:42]#[N:43])=[CH:11][CH:10]=1)(=O)CC.[OH-].[Li+]>O1CCOCC1.O>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([C:32]2[S:33][CH:34]=[C:30]([CH2:29][S:28][C:17]3[C:16]([C:42]#[N:43])=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][OH:5])=[CH:10][CH:11]=4)[C:24]4[C:23](=[O:25])[NH:22][C:21]([CH2:26][CH3:27])=[N:20][C:19]=4[N:18]=3)[N:31]=2)=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 136052982HCID 136052982, compound

Product 1

HCID 136052976HCID 136052976, compound

Reagents, catalysts & solvents 1

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

Procedure

40 mg (0.063 mmol) of 2-{4-[7-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-6-cyano-2-ethyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-5-yl]phenoxy}ethyl propanoate were initially charged in 4 ml of a dioxane/water mixture 2:1, 3 mg (0.127 mmol) of lithium hydroxide were added and the mixture was stirred at RT. After 3 h, the reaction mixture was purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5, with 0.1% TFA added). This gave 27 mg (70% of theory) of the target compound.

Workup

  1. additionwere added
  2. customthe reaction mixture was purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record
ord-cdb57be509af453991793de040288472
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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