Water → HCID 57527220, compound

HRID 1452992Notes

Reaction equation

HRID 1452992 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]2[N:18]=[C:17]3[S:19][C:20]([NH:22]C(=O)C4C=CC=CC=4)=[N:21][C:16]3=[CH:15][CH:14]=2)=[CH:11][N:10]([CH3:31])[N:9]=1.O.[OH-].[Na+]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]2[N:18]=[C:17]3[S:19][C:20]([NH2:22])=[N:21][C:16]3=[CH:15][CH:14]=2)=[CH:11][N:10]([CH3:31])[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 57527230HCID 57527230, compound

Product 1

HCID 57527220HCID 57527220, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-(5-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridine-2-yl)benzamide (0.36 g, 0.838 mmol, 1.0 eq.) in 70% aqueous H2SO4 (4.2 mL) was heated at 105° C. for 2 h. After cooling to room temperature, the reaction mixture was added to water. At 0° C., 30% aqueous NaOH followed by solid NaOH were added until pH ˜13 by litmus paper. The precipitate was washed with water and dried to give 5-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridine-2-amine as a tan solid (0.1493 g, 55% yield).

Workup

  1. customAt 0° C.
  2. additionwere added until pH ˜13 by litmus paper
  3. washThe precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-48dd00cc627f4c3cb41a297ce0c5bd0c
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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