Water → HCID 12147079, compound

HRID 2415695Notes

Reaction equation

HRID 2415695 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:23]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:13](=[O:14])[N:6]12)=[O:4].O.[Li+].[OH-]>CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[C:13](=[O:14])[N:6]3[CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH2:8][N:7]3[C:11]=2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:23]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 12147078HCID 12147078, compound

Product 1

HCID 12147079HCID 12147079, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-1-(2-phenoxy-pyrimidin-4-yl)-3-oxo-5,6,7,8-tetrahydro-3H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid methyl ester, 22, (0.02 g, 0.0143 mmol) in methanol (1 mL) and water (1 mL) is added LiOH (0.016 g, 0.65 mmol). The reaction solution is stirred at room temperature for 3 hours then quenched by the addition of 1 N HCl (20 mL). The reaction solution is extracted with ethyl acetate (3×50 mL), the organic layers are combined, washed with brine, dried, and concentrated in vacuo to afford 0.012 g (63% yield) of the desired product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.45 (dd, J=4.6, 2.1 Hz, 1 H), 7.14-7.44 (m, 7 H), 6.84-6.95 (m, 3 H), 4.93 (dd, J=11.7, 9.3 Hz, 1 H), 4.23 (br d, J=12.9 Hz, 1 H), 3.04-3.11 (m, 1H), 2.46-2.52 (m, 2 H), 1.71-1.93 (m, 2 H), APCI/MS: 447 (M+H).

Workup

  1. customthen quenched by the addition of 1 N HCl (20 mL)
  2. extractionThe reaction solution is extracted with ethyl acetate (3×50 mL)
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a3f6537fbb84e24a2709aaf219d1925
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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