Hydrochloric Acid → HCID 118021716, compound

HRID 575741Notes

Reaction equation

HRID 575741 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[Br:7][C:8]1[CH:9]=[C:10]([NH2:19])[CH:11]=[N:12][C:13]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1.N1C=CC=CC=1.Cl>C(Cl)Cl>[Br:7][C:8]1[CH:9]=[C:10]([NH:19][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:11]=[N:12][C:13]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 672819095-Bromo-6-(cyclopropylmethoxy)-3-pyridinamine

Product 1

HCID 118021716HCID 118021716, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylsulfonyl chloride (170 uL, 1.8 mmol) was added to a stirred solution of 5-bromo-6-(cyclopropylmethoxy)pyridin-3-amine (440 mg, 1.8 mmol) and pyridine (725 uL) in DCM (4.5 mL) at 0° C. under nitrogen. After the mixture was allowed to warm to rt and stir for 12 h, it was treated with 1N HCl (15 mL) and extracted with DCM (3×15 mL); the combined organic extracts were washed with saturated bicarbonate solution (aq), dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using a gradient of EtOAc (0 to 100%) in DCM to afford the title compound (181 mg, 88%) as a tan solid. LCMS (M+H)+=336.

Workup

  1. extractionextracted with DCM (3×15 mL)
  2. washthe combined organic extracts were washed with saturated bicarbonate solution (aq)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f231cd1f3834d38b485b376dac995c2
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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