Pyridine → HCID 178477711, compound

HRID 64161Notes

Reaction equation

HRID 64161 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:10][CH:11]=2)[N:3]=[N:2]1.N1C=CC=CC=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:7]=[C:8]3[N:14]=[CH:13][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)[C:9]3=[N:10][CH:11]=2)[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 178507288HCID 178507288, compound

Product 1

HCID 178477711HCID 178477711, compoundYield 9.3%

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, 0.179 mmol) in DCM was added pyridine (42 mg, 0.53 mmol, 3.0 eq.) followed by ethanesulfonyl chloride (20 mg, 0.179 mmol, 1.0 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 9.3% yield (8 mg). 1H NMR (300 MHz, DMSO): δ 10.4 (s, 1H) 9.0-8.97 (m, 2H), 8.64 (d, 1H), 7.92 (s, 1H), 7.75-7.64 (m, 3H), 7.47-7.43 (m, 3H), 3.31-3.24 (q, 2H), 1.39-1.34 (t, 3H); LC-MS (ESI): Calculated mass: 481.4; Observed mass: 481.8 [M+H]+ (rt: 1.36 min).

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 9.3% yield (8 mg)
  5. custom481.8 [M+H]+ (rt: 1.36 min)

Sources & evidence

ORD record
ord-10b23c71b85746fe8ce6097337d6dc6d
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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