Pyridine → HCID 51034014, compound

HRID 1889255Notes

Reaction equation

HRID 1889255 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([F:13])=[CH:4][C:3]=1[C:14]1[C:18]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH2:26][CH:27]([NH:29][C:30](=[O:33])[O:31][CH3:32])[CH3:28])[N:20]=2)=[CH:17][N:16]([CH:34]([CH3:36])[CH3:35])[N:15]=1.NC1C=CC=CC=1.N1C=CC=CC=1.CS(Cl)(=O)=O>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:6][C:5]([F:13])=[CH:4][C:3]=1[C:14]1[C:18]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH2:26][C@@H:27]([NH:29][C:30](=[O:33])[O:31][CH3:32])[CH3:28])[N:20]=2)=[CH:17][N:16]([CH:34]([CH3:36])[CH3:35])[N:15]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6115AnilineHCID 31297Methanesulfonyl chlorideHCID 75601906HCID 75601906, compound

Product 1

HCID 51034014HCID 51034014, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

S)-Methyl 1-(4-(3-(2-chloro-5-fluoro-3-(methanesulfonamido)phenyl)-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate. A mixture of the aniline product of step 1 (46 mg), pyridine (2 ml), triethylamine (1 mL), DCM (4 ml), and methanesulfonyl chloride (23 ul, 0.3 mmol) was stirred at rt for 16 h. The crude reaction mixture was concentrated, then the residue was taken up in a mixture of toluene (9 ml), ethanol (1 ml), sodium carbonate (2 g), and water (10 ml). The stirred mixture was heated at 85° C. for 16 h. Workup as for Step 1 provided the crude product, which was purified by silica gel chromatography (60:1 to 40:1 DCM/methanol eluant) to provide the title compound.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. additionthe residue was taken up in a mixture of toluene (9 ml), ethanol (1 ml), sodium carbonate (2 g), and water (10 ml)
  4. temperatureThe stirred mixture was heated at 85° C. for 16 h
  5. customWorkup as for Step 1 provided the crude product, which
  6. customwas purified by silica gel chromatography (60:1 to 40:1 DCM/methanol eluant)

Sources & evidence

ORD record
ord-8b23cd45496c4c468fb57cfd7ea66125
Source dataset
uspto-grants-2013_08
Patent number
US08501758B2

Reaction notes

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