Methanesulfonyl chloride → HCID 71542173, compound

HRID 1776501Notes

Reaction equation

HRID 1776501 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N+:5]([O-:43])[CH:6]=[C:7]([Cl:42])[C:8]=1[CH2:9][C@@H:10]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[C:29]([O:37][CH2:38][CH:39]2[CH2:41][CH2:40]2)[CH:28]=1)[O:11][C:12](=[O:26])[CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl.Cl>[Cl:42][C:7]1[CH:6]=[N+:5]([O-:43])[CH:4]=[C:3]([Cl:2])[C:8]=1[CH2:9][C@@H:10]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]([F:36])[F:35])=[C:29]([O:37][CH2:38][CH:39]2[CH2:40][CH2:41]2)[CH:28]=1)[O:11][C:12](=[O:26])[CH2:13][N:14]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[S:45]([CH3:44])(=[O:47])=[O:46]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86679448HCID 86679448, compound

Product 1

HCID 71542173HCID 71542173, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(3,4-dimethoxybenzylamino)acetoxy)ethyl)pyridine 1-oxide hydrochloride (42 mg, 0.064 mmol) was dissolved in DCM (1.5 ml). Py (500 μl, 6.18 mmol) and methanesulfonyl chloride (5.96 μl, 0.076 mmol) were added, and the reaction was stirred at RT for 2 hours to achieve completion. The reaction mixture was diluted with HCl 1M and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by preparative reverse-phase HPLC to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(N-(3,4-dimethoxybenzyl)methylsulfonamido)-acetoxy)ethyl)pyridine 1-oxide (20 mg, 44.5% yield).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-4cb0907f362b43408b8cb5e7e89754b4
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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