Pyridine → HCID 86679426, compound

HRID 1776469Notes

Reaction equation

HRID 1776469 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>[NH4+].[Cl-]>[CH3:19][O:18][C:17]1[CH:16]=[CH:15][C:4]([CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:3][C:2]=1[NH:1][S:27]([CH3:26])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86679425HCID 86679425, compound

Product 1

HCID 86679426HCID 86679426, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-amino-4-methoxybenzyl(methyl)carbamate (265.3 mg, 0.996 mmol) was dissolved in pyridine (3000 μl, 37.1 mmol) and cooled to 0° C. MsCl (93 μl, 1.195 mmol) was added dropwise, and the reaction was stirred at RT for 1 hour. The solution was diluted with NH4Cl sat. sol. and extracted twice with DCM. The organic layers were washed with brine, dried over Na2SO4 and evaporated under vacuum to give tert-butyl 4-methoxy-3-(methylsulfonamido)benzyl(methyl)-carbamate (249.5 mg, 0.724 mmol, 72.7% yield, MS/ESI+ 367.2 [MNa]+) that was used in the next step without further purification.

Workup

  1. extractionextracted twice with DCM
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-2fdb7f44540240ffa72963ce96367ad1
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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