Pyridine → HCID 67070129, compound

HRID 2390842Notes

Reaction equation

HRID 2390842 reaction equation
[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([CH2:19][CH2:20][C:21]2[N:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([CH2:19][CH2:20][C:21]2[N:26]=[CH:25][C:24]([NH:27][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67070164HCID 67070164, compound

Product 1

HCID 67070129HCID 67070129, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

step 3—To a solution of 182 (0.183 g, 0.467 mmol), pyridine (0.076 mL, 0.935 mmol) and DCM (5 mL) was added dropwise methanesulfonyl chloride (0.268 g, 2.337 mmol). The reaction was stirred overnight at RT then evaporated and taken up in EtOAc, washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient to afford 0.099 g of N-(6-{2-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-pyridin-3-yl)-methanesulfonamide (184) along with the bis-mesylated byproduct.

Workup

  1. customthen evaporated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient

Sources & evidence

ORD record
ord-76aa5c3d0fe84207bbf3e2b22ee2e2a6
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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