Dimethyl Sulfate → tert-butyl-N-methyl-N-[1-[[5-[methyl(oxane-4-carbonyl)amino]-6-(2-phenyl-ethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

HRID 535439Notes

Reaction equation

HRID 535439 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:39])[N:9]([CH3:38])[CH:10]([CH3:37])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[C:16]([C:29]#[C:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:15]=1)=[O:12])([CH3:6])([CH3:5])[CH3:4].[CH3:40]OS(OC)(=O)=O>C1COCC1>[C:3]([O:7][C:8](=[O:39])[N:9]([CH3:38])[CH:10]([CH3:37])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:40])[C:21]([CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[O:22])=[C:16]([C:29]#[C:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:15]=1)=[O:12])([CH3:5])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 86694390tert-butyl-N-methyl-N-[1-[[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Product 1

HCID 86694429tert-butyl-N-methyl-N-[1-[[5-[methyl(oxane-4-carbonyl)amino]-6-(2-phenyl-ethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT NaH (60% dispersion in mineral oil, 2.3 mg, 0.0.06 mmol) is added to tert-butyl-N-methyl-N-[1-[[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate E5b (35 mg, 0.04 mmol) in THF (1 ml). After stirring for 10 minutes dimethylsulfate (4 μl, 0.06 mmol) is added to the mixture and stirring continued for 20 minutes. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 5 mg (23%). HPLC-MS: M+H=521; tR=2.06 min (*Method—2).

Workup

  1. additionis added to the mixture
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-c8b67e50d4d14b7a883374dfc0be6981
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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