Propylamine → HCID 57527189, compound

HRID 1671826Notes

Reaction equation

HRID 1671826 reaction equation
Br[C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[N:13][N:14]([CH3:16])[CH:15]=1)[N:5]=2.[CH2:24]([NH2:27])[CH2:25][CH3:26]>O1CCOCC1.C(Cl)Cl>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:12]1[C:11]([C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:27][CH2:24][CH2:25][CH3:26])=[N:10][C:9]3=[CH:8][CH:7]=2)=[CH:15][N:14]([CH3:16])[N:13]=1

Participants

5

Reactant 2

HCID 7852PropylamineHCID 57527193HCID 57527193, compound

Product 1

HCID 57527189HCID 57527189, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-bromo-5-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridine (0.0294 g, 0.0755 mmol, 1.0 eq.) and n-propylamine (0.1 mL, 1.22 mmol, 16.1 eq.) in 1,4-dioxane (1.5 mL) was heated at 75° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-N-propylthiazolo[5,4-b]pyridine-2-amine as a light tan solid (0.0270 g, 97% yield). LC/MS (MH)= 368.16.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64351507fb0b4f1bb9e7046136f0cf91
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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