Hydrochloric Acid → 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylic acid

HRID 2234044Notes

Reaction equation

HRID 2234044 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:21]=[C:20]([C:30]([O:32]C)=[O:31])[CH:19]=2)[CH2:14][CH2:13]1)=[O:10].[OH-].[Li+].Cl>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[N:23]=[C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:21]=[C:20]([C:30]([OH:32])=[O:31])[CH:19]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68581162Methyl 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylate

Product 1

HCID 685800486-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylate (Example 9, 224 mg, 0.45 mmol) was dissolved in MeOH (5 ml). 2 N lithium hydroxide (2 ml) was added and the reaction was stirred at room temperature for 3 h. The mixture was acidified with 1 N HCl and was extracted with EtOAc (3×50 ml), dried over Na2SO4 and concentrated in vacuo to provide 200 mg of the title compound.

Workup

  1. extractionwas extracted with EtOAc (3×50 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0914202334c47b39cf838662b0e27f3
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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