Pyridine → HCID 90281516, compound

HRID 2170371Notes

Reaction equation

HRID 2170371 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Br:37])[C:5]([C@@H:8]([NH:18][C:19](=[O:36])[CH2:20][N:21]2[C:25]3[C:26]([F:31])([F:30])[C@@H:27]4[CH2:29][C@@H:28]4[C:24]=3[C:23]([C:32]([F:35])([F:34])[F:33])=[N:22]2)[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][CH:7]=1.N1C=CC=CC=1.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[Br:37][C:4]1[C:5]([C@@H:8]([NH:18][C:19](=[O:36])[CH2:20][N:21]2[C:25]3[C:26]([F:31])([F:30])[C@@H:27]4[CH2:29][C@@H:28]4[C:24]=3[C:23]([C:32]([F:33])([F:34])[F:35])=[N:22]2)[CH2:9][C:10]2[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=2)=[N:6][CH:7]=[C:2]([NH:1][S:45]([CH3:44])(=[O:47])=[O:46])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 90281431HCID 90281431, compound

Product 1

HCID 90281516HCID 90281516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 41C (35.6 mg, 0.06 mmol) was dissolved in 1 mL of methylene chloride and cooled to 0° C. To it was added 0.2 mL of pyridine followed by methanesulfonyl chloride (0.007 mL, 0.09 mmol). The reaction mixture was stirred at 0° C. for one hour. LCMS showed complete reaction. It was then partitioned between EtOAc and brine. The organic layer was separated, dried and concentrated to afford the title product. MS (m/z) 670.27 [M+H]+.

Workup

  1. customreaction
  2. customIt was then partitioned between EtOAc and brine
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ff334f34e7e441fa0855bbdfe348843
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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