Glycidol → 3-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propane-1,2-diol

HRID 1401774Notes

Reaction equation

HRID 1401774 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:15]=[C:16]([N:19]4[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]4)[S:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[O:27]1[CH2:31][CH:28]1[CH2:29][OH:30]>CN(C=O)C>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3[N:15]=[C:16]([N:19]4[CH2:24][CH2:23][CH:22]([NH:25][CH2:31][CH:28]([OH:27])[CH2:29][OH:30])[CH2:21][CH2:20]4)[S:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 11164GlycidolHCID 53312200HCID 53312200, compound

Product 1

HCID 533123673-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.41 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine were dissolved in 2 ml of DMF, and 27.4 μl (0.41 mmol) of 2,3-epoxy-1-propanol were added. The reaction mixture was irradiated in the microwave at 120° C. for 3 h and subsequently stripped off to dryness. The residue was purified by means of flash chromatography on silica gel.

Workup

  1. customThe reaction mixture was irradiated in the microwave at 120° C. for 3 h
  2. customThe residue was purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-b2ac3d3c3e324bc8ab050d6ce2442294
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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