Tetrahydrofuran → 2-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid

HRID 2066874Notes

Reaction equation

HRID 2066874 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:31]([F:34])([F:33])[F:32])=[N:7][C:8]([N:11]2[CH2:16][CH2:15][C:14](=[N:17][O:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:13][CH2:12]2)=[N:9][CH:10]=1)=[O:4].C1COCC1.[OH-].[Na+]>Cl>[CH:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([O:18][N:17]=[C:14]2[CH2:13][CH2:12][N:11]([C:8]3[N:7]=[C:6]([C:31]([F:33])([F:34])[F:32])[C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=3)[CH2:16][CH2:15]2)[CH2:20][CH2:21]1)=[O:26])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866550152-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 866550162-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

The crude 57a obtained in the previous step was taken up with THF (3 mL) and 1N NaOH (0.6 mL) and heated to 50° C. for 2 h. The mixture was cooled, diluted with 10 mL of 1N HCl and extracted with DCM (3×5 mL). The combined extracts were dried and concentrate to afford the crude 57b.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with DCM (3×5 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-fc704f14dd4544c3bfc6c5180a261381
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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