Hydrochloric Acid → HCID 11419653, compound

HRID 890430Notes

Reaction equation

HRID 890430 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH3:33])[CH2:15][C:16]3[C:17]([CH3:32])=[N:18][C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[N:20][CH:21]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[OH-].[Li+].Cl>C1COCC1.CCOC(C)=O>[CH3:33][N:14]([CH2:15][C:16]1[C:17]([CH3:32])=[N:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=2)=[N:20][CH:21]=1)[C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]([OH:34])=[O:2])[CH:6]=[CH:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69637826HCID 69637826, compound

Product 1

HCID 11419653HCID 11419653, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

70 mg (0.15 mmol) (5-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-amino}-indol-1-yl)-acetic acid methyl ester and 0.3 ml 1N lithium hydroxide solution were stirred for 2 h in 0.5 ml THF at RT. To the reaction mixture was added 0.6 ml 1N HCl and then the mixture was taken up in AcOEt and washed with water. The crude product was suspended in ether/heptane 1:19. The resulting crystals were filtered off to provide 47 mg of pure (5-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-amino}-indol-1-yl)-acetic acid.

Workup

  1. washwashed with water
  2. filtrationThe resulting crystals were filtered off

Sources & evidence

ORD record
ord-9e3fc7d609714acfa8036484c48e684f
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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