Hydrochloric Acid → HCID 57737209, compound

HRID 1157566Notes

Reaction equation

HRID 1157566 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23]C(=O)C(F)(F)F)[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH3:30][N:31]([CH2:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37])[CH3:32].Cl>O1CCOCC1.CC(O)C>[NH2:23][C:19]1[CH:18]=[C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:37][C:36]4[CH:38]=[CH:39][CH:40]=[C:34]([CH2:33][N:31]([CH3:30])[CH3:32])[CH:35]=4)[N:7]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 992943-amino-N,N-dimethylbenzylamineHCID 59513717N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 57737209HCID 57737209, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (3.0 g, 0.007 mols) (see Example 1, Step C) in 1,4-dioxane (60 mL) and i-PrOH (60 mL) was added 3-[(dimethylamino)methyl]aniline (1.61 g, 0.011 mol) followed by catalytic 12M HCl. After heating four days at 90° C., reaction was quenched with saturated NaHCO3 (100 mL), solvent removed by rotary evaporation, aqueous layer extracted with DCM (3×200 mL), organic layers concentrated, and purified by column chromatography (0-100% 9:1:0.1 DCM:MeOH:NH4OH) to provide the product (1.25 g, 40%) as tan foam. ES-LC/MS m/z=436 [M+H]+.

Workup

  1. customreaction
  2. customwas quenched with saturated NaHCO3 (100 mL), solvent
  3. customremoved by rotary evaporation, aqueous layer
  4. extractionextracted with DCM (3×200 mL), organic layers
  5. concentrationconcentrated
  6. custompurified by column chromatography (0-100% 9:1:0.1 DCM:MeOH:NH4OH)

Sources & evidence

ORD record
ord-80a6be733c5b4ddf94ccbaa233a5b386
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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