Methyl iodide → {(R)-3-[(6-Chloro-benzooxazol-2-yl)-methyl-amino]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanone

HRID 598505Notes

Reaction equation

HRID 598505 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([NH:9][CH:10]3[CH2:14][CH2:13][N:12]([C:15]([C:17]4[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=4[O:25][CH3:26])=[O:16])[CH2:11]3)[O:8][C:4]=2[CH:3]=1.CI.[C:31]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]([CH3:31])[C@@H:10]3[CH2:14][CH2:13][N:12]([C:15]([C:17]4[C:18]([O:25][CH3:26])=[CH:19][CH:20]=[CH:21][C:22]=4[O:23][CH3:24])=[O:16])[CH2:11]3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53232364[3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-(2,6-dimethoxy-phenyl)-methanone

Product 1

HCID 57748846{(R)-3-[(6-Chloro-benzooxazol-2-yl)-methyl-amino]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanoneYield 461%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 20 mg (0.05 mmol) [3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-(2,6-dimethoxy-phenyl)-methanone (example 1), 353 mg (2.48 mmol) methyliodid and 10 mg (0.075 mmol) K2CO3 in 0.5 mL DMF was stirred at 75° C. The mixture was concentrated, water and methanol was added and the mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 9.6 mg (461%) of the title compound as light yellow solid. (MH+) 418.1.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater and methanol was added
  3. customthe mixture was subjected to purification by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and formic acid
  6. additionThe product containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-cc3b09fcc0c64cc79384cc3b2a17ce55
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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