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

HRID 1354311Notes

Reaction equation

HRID 1354311 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. temperaturethen cooled
  2. additionOn addition
  3. customthe acid precipitated from solution
  4. filtrationwas filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-33d4eb86f28947a7bf4d3865ac8af5f2
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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