Pyridine → HCID 178477710, compound

HRID 64156Notes

Reaction equation

HRID 64156 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]3[N:14]=[CH:13][N:12]([C:15]4[CH:16]=[C:17]([NH2:29])[CH:18]=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=5[F:28])[CH:20]=4)[C:9]3=N[CH:11]=2)[N:3]=[N:2]1.N1C=CC=C[CH:31]=1.[CH2:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37]>C(Cl)Cl>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:31][C:9]3[N:12]([C:15]4[CH:16]=[C:17]([NH:29][S:38]([CH2:36][CH3:37])(=[O:40])=[O:39])[CH:18]=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=5[F:28])[CH:20]=4)[CH:13]=[N:14][C:8]=3[CH:7]=2)[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 178507288HCID 178507288, compound

Product 1

HCID 178477710HCID 178477710, compoundYield 2.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(6-(1H-1,2,3-triazol-4-yl)-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-amine (70 mg, 0.18 mmol) in DCM was added pyridine (42 mg, 0.54 mmol, 3.0 eq.) followed by ethanesulfonyl chloride (27 mg, 0.216 mmol, 1.2 eq.). The reaction was monitored by LCMS. After completion of the reaction the solvent was distilled off and the crude product was purified by preparative HPLC to give the product in 2.3% yield (2 mg).

Workup

  1. customAfter completion of the reaction the solvent
  2. distillationwas distilled off
  3. customthe crude product was purified by preparative HPLC
  4. customto give the product in 2.3% yield (2 mg)

Sources & evidence

ORD record
ord-96f84616f81e4bcc954d1697df60a400
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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