Water → HCID 72549437, compound

HRID 518323Notes

Reaction equation

HRID 518323 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])=[C:6]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.[CH2:25]([S:27](Cl)(=[O:29])=[O:28])[CH3:26].O>C(Cl)Cl>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[O:16][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:27]([CH2:25][CH3:26])(=[O:29])=[O:28])=[CH:7][C:6]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 90025866HCID 90025866, compound

Product 1

HCID 72549437HCID 72549437, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 5-[5-amino-2-(2,4-difluorophenoxyl)phenyl]-1-methylpyridin-2-one (30 mg, 0.09 mmol) in DCM (4 mL) was added TEA (27.3 mg, 0.27 mmol) and EtSO2Cl (35.39 mg, 0.27 mmol). The mixture was stirred at 30° C. for 12 h. Water (4 mL) was added and the mixture was extracted with DCM (4 mL×3). The organic layer was concentrated and the residue was purified by prep-HPLC to give the title compound (10 mg, 26%) as light yellow gum. 1H NMR (CDCl3, 400 MHz) δ7.68-7.66 (m, 2H), 7.28 (d, J=2.4 Hz, 1H), 7.13-7.10 (m, 1H), 7.09 (s, 1H), 7.00-6.92 (m, 2H), 6.84-6.86 (m, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.73 (d, J=9.2 Hz, 1H), 3.65 (s, 3H), 3.14 (q, J=7.2 Hz, 2H), 1.41 (t, J=7.2 Hz, 3H). LCMS (M+H)+ 421.

Workup

  1. extractionthe mixture was extracted with DCM (4 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-78b6147be4c3444fb352c68ff39b343b
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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