HCID 67441926, compound → HCID 67438844, compound

HRID 1890255Notes

Reaction equation

HRID 1890255 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[N:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=23)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>S(=O)(=O)(O)O>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:16]2[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=3)=[C:19]3[CH2:20][CH2:21][CH2:22][CH2:23][N:18]3[N:17]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 67441926HCID 67441926, compound

Product 1

HCID 67438844HCID 67438844, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

With ice-cooling, 10 ml of conc. sulphuric acid are added to 1.29 g (1.29 mmol) of N-benzyl-4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl]pyridine-2-amine, and the mixture is stirred at room temperature for 1 h. The reaction mixture is stirred into ice-water, adjusted to pH 10 using cone. NaOH and extracted with 3×50 ml of dichloromethane. The combined organic phases are washed with water, dried over MgSO4 and freed from the solvent under reduced pressure. This gives 239 mg (35%) of the desired product; log P(HCOOH): 1.21; 1H-NMR (DMSO-d6): 7.81 (d, 1H), 7.416 (dd, 2H), 7.15 (dd, 2H), 6.28 (s, 1H), 6.24 (d, 1H), 5.83 (br.s, 2H), 4.15 (dd, 2H), 2.73 (dd, 2H), 2.02 (m, 2H), 1.80 (m, 2H).

Workup

  1. temperatureWith ice-cooling
  2. extractionNaOH and extracted with 3×50 ml of dichloromethane
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d21804c6bb2344b995f54f5fddf1cc28
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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