Methylamine → HCID 68578852, compound

HRID 2047329Notes

Reaction equation

HRID 2047329 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:28]=[C:27]([CH3:29])[C:18]([O:19][CH2:20][CH2:21]OS(C)(=O)=O)=[C:17]([CH2:30][CH3:31])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:32])[N:5]=1)[CH3:2].[CH3:35][NH2:36]>CO>[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:28]=[C:27]([CH3:29])[C:18]([O:19][CH2:20][CH2:21][NH:36][CH3:35])=[C:17]([CH2:30][CH3:31])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:32])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86640601HCID 86640601, compound

Product 1

HCID 68578852HCID 68578852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude methanesulfonic acid 2-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethyl ester (110 mg, 0.225 mmol, Example 55 step a)) in 8 M methylamine in methanol (4 mL) is stirred in a sealed glass vial at 70° C. for 15 h. The solvent is evaporated and the crude product is purified on prep. TLC plates using DCM containing 10% of 7 N NH3 in methanol to give the title compound (93 mg) as a pale yellow oil; LC-MS: tR=0.71 min; [M+1]+=424.19.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified on prep

Sources & evidence

ORD record
ord-929d46d1e31440df9bb9c20c49334079
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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