Hydrochloric Acid → HCID 178428572, compound

HRID 1716521Notes

Reaction equation

HRID 1716521 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]([CH3:32])[C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=4)[N:19]=3)=[CH:16][N:17]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl.C(Cl)(Cl)Cl.C(OCC)C>CO.O1CCCC1>[CH3:32][N:12]([CH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1)[C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=3)[N:19]=2)=[CH:16][N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21911965Chloroform etherHCID 178501120HCID 178501120, compound

Product 1

HCID 178428572HCID 178428572, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-4-[(N-methyl-N-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}amino)methyl]cyclohexanecarboxylic acid methyl ester (217 mg, 0.48 mmol) obtained in Step 5, 1N aqueous sodium hydroxide (2 ml, 2 mmol) in methanol (2 ml) and tetrahydrofuran (2 ml) was stirred at room temperature for 16 hours. The solution was neutralized with 1N hydrochloric acid and extracted with chloroform (50 ml×2). The organic layer was washed with a saturated brine (20 ml) and dried over magnesium sulfate and filtrated and vacuum concentrated. The solid obtained by adding chloroform-diethyl ether (1:1) (10 ml) to the residue was collected by filtration, dried in vacuo and thereby trans-4-[(N-methyl-N-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}amino)methyl]cyclohexanecarboxylic acid (190 mg, 90%) was obtained.

Workup

  1. extractionextracted with chloroform (50 ml×2)
  2. washThe organic layer was washed with a saturated brine (20 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationvacuum concentrated
  6. customThe solid obtained
  7. filtrationwas collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0191a580cfe5420c903789d9f97a1f14
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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