Methanesulfonyl chloride → HCID 71735774, compound

HRID 525599Notes

Reaction equation

HRID 525599 reaction equation
[NH2:1][C@H:2]([CH2:23][F:24])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)[OH:4].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(OC(=O)C)C.O>[F:24][CH2:23][C@@H:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[C@H:3]([OH:4])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[N:15][C:14]([CH2:17][NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86695483HCID 86695483, compound

Product 1

HCID 71735774HCID 71735774, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of N-((5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)phenyl)pyridin-2-yl)methyl)methanesulfonamide (100 mg, 0.28 mmol) in ethylacetate/aqueous NaHCO3 (1:1) (2 mL) is slowly added methanesulfonyl chloride (50 mg, 0.42 mmol) over a period of 20 minutes. Reaction is diluted with water (2 mL) and extracted with ethylacetate (3×5 mL). Combined organic solution is dried over Na2SO4 and concentrated. Crude product is purified using HPLC to give the title compound (60 mg): 1H NMR (400 MHz, DMSO-d6) 2.55 (s, 3H), 2.98 (s, 3H), 3.67-3.80 (m, 1H), 4.18-4.26 (m, 0.5H), 4.31-4.40 (m, 2.5H), 4.48-4.55 (m, 0.5H), 4.60-4.67 (m, 0.5H), 4.80-4.87 (m, 1H), 5.83-5.93 (m, 1H), 7.27 (d, 1H), 7.54 (d, 2H), 7.54 (d, 1H), 7.62 (d, 1H), 7.70-7.79 (m, 3H), 8.20-8.26 (m, 1H), 8.90 (d, 1H). m/z (Cl) M+H 432.

Workup

  1. customof 20 minutes
  2. customReaction
  3. extractionextracted with ethylacetate (3×5 mL)
  4. dry with materialCombined organic solution is dried over Na2SO4
  5. concentrationconcentrated
  6. customCrude product is purified

Sources & evidence

ORD record
ord-463cfe923e61479280386b6f36bab321
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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