Hydrochloric Acid → HCID 58883458, compound

HRID 1765767Notes

Reaction equation

HRID 1765767 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:21]3[CH:20]([N:24]([CH:26]4[CH2:28][CH2:27]4)[CH3:25])[CH2:19][CH2:18][C:17]([CH3:30])([CH3:29])[C:16]=3[CH:15]=2)=[O:12])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[CH:26]1([N:24]([CH3:25])[CH:20]2[CH2:19][CH2:18][C:17]([CH3:29])([CH3:30])[C:16]3[CH:15]=[C:14]([NH:13][C:11](=[O:12])[NH:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=4)[CH:23]=[CH:22][C:21]2=3)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69078191HCID 69078191, compound2×

Product 1

HCID 58883458HCID 58883458, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{3-[5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-ureido}-benzoic acid methyl ester (Intermediate 59, 0.045 g, 0.106 mmol) in methanol (2 mL) and tetrahydrofuran (3 mL) was treated with a 2M solution of sodium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was neutralized with 5% aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford a solid that was recrystallized from hot acetonitrile to afford the title product as a white solid (0.012 g, 28%).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a solid
  8. customthat was recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-70cafa34320d4554b1c71f99ad155a6b
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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