Sodium Carbonate → 2-{1-[4-(3,3-Dimethylindan-5-yl)thiazol-2-yl]piperidin-4-ylamino}-ethanol

HRID 1401853Notes

Reaction equation

HRID 1401853 reaction equation
Br[C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:8]2)[S:5][CH:6]=1.[CH3:17][C:18]1([CH3:36])[C:26]2[C:21](=[CH:22][CH:23]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[CH3:17][C:18]1([CH3:36])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:2]3[N:3]=[C:4]([N:7]4[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:8]4)[S:5][CH:6]=3)[CH:25]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 673233402-(1-(4-Bromothiazol-2-yl)piperidin-4-ylamino)ethanolHCID 673240062-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 533115392-{1-[4-(3,3-Dimethylindan-5-yl)thiazol-2-yl]piperidin-4-ylamino}-ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

130 mg (0.30 mmol) of 2-[1-(4-bromothiazol-2-yl]piperidin-4-ylamino]ethanol from step b, 92 mg (0.29 mmol) of 2-(3,3-dimethylindan-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 92 mg (0.03 mmol) of tetrakis(triphenlyphosphine)palladium(0) and 125 mg (1.18 mmol) of sodium carbonate were weighed out, placed under nitrogen. 2.5 ml of dioxane and 0.5 ml of water were added with stirring. The mixture was degassed, homogenised in an ultrasound bath and heated at 120° C. in the microwave for 30 min, diluted with about 20 ml of EA and 20 ml of water and filtered off. The phases were separated, and the water phase was extracted a further once with EA. The organic phases were combined, dried over sodium sulfate, filtered and evaporated. The oily residue was purified by means of preparative HPLC. The product is in the form of the hydrochloride.

Workup

  1. customThe mixture was degassed
  2. stirringhomogenised in an ultrasound bath
  3. additiondiluted with about 20 ml of EA and 20 ml of water
  4. filtrationfiltered off
  5. customThe phases were separated
  6. extractionthe water phase was extracted a further once with EA
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-4222cf8f7f8b4004b3e376aef5e1af2c
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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