Triethylamine → HCID 46837117, compound

HRID 1520227Notes

Reaction equation

HRID 1520227 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.CCN(CC)CC.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](Cl)=[O:34].N1C=CC=CC=1C=O>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:15]=[N:16][N:17]([C:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=2)=[O:34])[CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 142732-PyridinecarboxaldehydeHCID 135033Picolinoyl Chloride HydrochlorideHCID 25138329HCID 25138329, compound

Product 1

HCID 46837117HCID 46837117, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

According to Scheme 21: To a solution of 5-methyl-4-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-2-amine (0.19 mmol, 50 mg) in DCM (2 mL) was added Et3N (0.78 mmol, 108 μL). After stirring for 10 minutes, picolinoyl chloride hydrochloride (0.39 mmol, 69.2 mg) was added. The reaction mixture was stirred for 3 hours at room temperature. The solvent was then removed under reduced pressure to afford a yellow solid. The crude mixture was solubilised in DMF. A white solid was precipitated, was filtered and was washed with MeOH. After evaporation, 4-(5-methyl-2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazol-1-yl)(pyridin-2-yl)methanone (50 μmol, 18 mg, 25%) was obtained as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at room temperature
  2. customThe solvent was then removed under reduced pressure
  3. customto afford a yellow solid
  4. customA white solid was precipitated
  5. filtrationwas filtered
  6. washwas washed with MeOH
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-df155eeab4044711a2e35fca170c88d0
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

Loading…