Pyridine → HCID 67958066, compound

HRID 1892567Notes

Reaction equation

HRID 1892567 reaction equation
[CH2:1]([NH:3][C:4]1[C:23]([C:24]2[CH:29]=[CH:28][C:27](OC)=[C:26]([C:32](=[O:44])[NH:33][C:34]3([C:38]4[N:43]=[CH:42][CH:41]=[CH:40][N:39]=4)[CH2:37][O:36][CH2:35]3)[CH:25]=2)=[CH:22][C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=1)[CH3:2].N1C=CC=CC=1.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>CN(C1C=CN=CC=1)C.O>[CH2:1]([N:3]([C:4]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:32](=[O:44])[NH:33][C:34]3([C:38]4[N:43]=[CH:42][CH:41]=[CH:40][N:39]=4)[CH2:37][O:36][CH2:35]3)[CH:25]=2)=[CH:22][C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=1)[S:52]([CH3:51])(=[O:54])=[O:53])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67959595HCID 67959595, compound

Product 1

HCID 67958066HCID 67958066, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 6-(ethylamino)-2-(4-fluorophenyl)-5-(4-methoxy-3-((3-(pyrimidin-2-yl)oxetan-3-yl)carbamoyl)phenyl)-N-methylbenzofuran-3-carboxamide (90 mg, 0.151 mmol), pyridine (5.0 mL), DMAP (18.46 mg, 0.151 mmol) and methanesulfonyl chloride (0.018 mL, 0.227 mmol) was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with EtOAc (20 ml×2). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by prep HPLC.

Workup

  1. extractionextracted with EtOAc (20 ml×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-52fd17f713014ff0b85a5aaa48dee3bd
Source dataset
uspto-grants-2013_08
Patent number
US08507683B2

Reaction notes

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