Ethanolamine → HCID 68503865, compound

HRID 2069463Notes

Reaction equation

HRID 2069463 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[OH:5][CH:6]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:31][CH:32]([CH3:34])[CH3:33])[N:25]=3)[O:21][N:20]=2)=[CH:15][CH:14]=1)[CH2:7]OS(C)(=O)=O>O1CCOCC1>[OH:2][CH2:1][CH2:3][NH:4][CH2:7][CH:6]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:31][CH:32]([CH3:34])[CH3:33])[N:25]=3)[O:21][N:20]=2)=[CH:15][CH:14]=1)[OH:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 87479192HCID 87479192, compound

Product 1

HCID 68503865HCID 68503865, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethanolamine (3.0 mL, 49.85 mmol) is added to a solution of methanesulfonic acid 2-hydroxy-2-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl ester (152 mg, 0.35 mmol) in dioxane (2.0 mL). The reaction mixture is stirred at 80° C. for 18 h, is then evaporated and purified by prep. TLC (eluting with DCM/MeOH 10:1) to give 99 mg of the title compound as a yellow oil; LC-MS: tR=0.74 min; [M+H]+=399.07. 1H NMR (CDCl3) δ 1.29 (d, J=6.5 Hz, 6H), 2.48 (s, 3H), 2.84 (m, 3H), 2.97 (dd, J=12.3, 3.5 Hz, 1H), 3.73 (t, J=5.0 Hz, 1H), 4.31 (m, 1H), 4.85 (dd, J=8.8, 3.3 Hz, 1H), 5.30 (s br, 1H), 7.29 (s, 1H), 7.53 (d, J=8.3 Hz, 2H), 8.17 (d, J=8.0 Hz, 2H).

Workup

  1. customis then evaporated
  2. custompurified by prep
  3. washTLC (eluting with DCM/MeOH 10:1)

Sources & evidence

ORD record
ord-ed78021b82c947beac49510992e516ab
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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