Hydrochloric Acid → 4-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid

HRID 1010844Notes

Reaction equation

HRID 1010844 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[C:9]([NH:10][C:11]2[C:16]3[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19][C:15]=3[N:14]=[C:13]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=3[F:29])[N:12]=2)=[CH:8][CH:7]=[N:6][CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]([F:29])=[C:22]([C:13]2[N:12]=[C:11]([NH:10][C:9]3[C:4]([C:3]([OH:30])=[O:2])=[CH:5][N:6]=[CH:7][CH:8]=3)[C:16]3[CH2:17][C:18]([CH3:20])([CH3:21])[CH2:19][C:15]=3[N:14]=2)[CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 588660424-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid methyl ester

Product 1

HCID 211043294-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acidYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid methyl ester (178 mg, 0.42 mmol) in dioxane (10 mL) was added NaOH (aq.) (451 μL, 0.44 mmol, 0.97N solution). The mixture was heated at 60° C. for 1 h, then cooled, and HCl (aq.) (425 μL, 0.44 mmol, 1.03N solution) was added. On addition, the acid precipitated from solution and was filtered and dried in vacuo, to give 137 mg of product.

Workup

  1. temperaturecooled
  2. additionOn addition
  3. customthe acid precipitated from solution
  4. filtrationwas filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-71797b8a9caf45288901f86e62633230
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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