Hydrochloric Acid → HCID 178525763, compound

HRID 1947000Notes

Reaction equation

HRID 1947000 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[N:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].C1COCC1.Cl>CO>[N:19]1([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C@H:9]3[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[N:18]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178472431HCID 178472431, compound

Product 1

HCID 178525763HCID 178525763, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-4-(4-indazol-1-ylpyrimidin-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (2.88 g, 7.9 mmol), aqueous NaOH (2 M, 65 mL) and THF (65 mL) was stirred overnight. MeOH (40 mL) was added, and the reaction mixture stirred for an additional 105 min. Aqueous HCl (1M) was added to reach pH 3, and the resulting solid collected by filtration to give trans-4-(4-indazol-1-yl-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid (2.739 g) without further purification.

Workup

  1. stirringthe reaction mixture stirred for an additional 105 min
  2. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-5bd5f3261076411c8277e8099e493a9e
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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