Lithium Hydroxide → HCID 86608278, compound

HRID 2233928Notes

Reaction equation

HRID 2233928 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[C:23]([Cl:25])[N:22]=[C:21]([C:26]([O:28]C)=[O:27])[CH:20]=3)[CH2:15][CH2:14]2)=[O:11])[NH:7][C:8]=1[CH3:9]>CO>[Br:3][C:4]1[CH:5]=[C:6]([C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[C:23]([Cl:25])[N:22]=[C:21]([C:26]([OH:28])=[O:27])[CH:20]=3)[CH2:15][CH2:14]2)=[O:11])[NH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86608279HCID 86608279, compound

Product 1

HCID 86608278HCID 86608278, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Lithium hydroxide (2 M, 4 ml) was warmed to 40° C. and a solution of methyl 6-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-chloropyrimidine-4-carboxylate (Example 73, 0.180 g, 0.394 mmol) in MeOH was added. The reaction was stirred at 40° C. for 30 mins. The MeOH was removed and the aqueous solution was cooled to 0° C. and it was acidified with 6 M HCl. The acidic solution was extracted with EtOAc, dried over MgSO4 and concentrated to give pink solid (0.15 g, 86%). An analytical sample was purified by reversed phase HPLC (acetonitrile/water (0.1% TFA), 20-95%).

Workup

  1. customThe MeOH was removed
  2. temperaturethe aqueous solution was cooled to 0° C.
  3. extractionThe acidic solution was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9fd0ffa539784f75853be7828df09a00
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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