Diethyl Ether → HCID 54596658, compound

HRID 1429551Notes

Reaction equation

HRID 1429551 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:40]=[CH:39][C:19]3[N:20]=[C:21]([O:23][CH:24]4[CH2:29][CH2:28][N:27]([C:30]5[N:35]=[CH:34][C:33]([CH2:36][CH2:37][CH3:38])=[CH:32][N:31]=5)[CH2:26][CH2:25]4)[S:22][C:18]=3[CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])=[O:8].CCO[CH2:44][CH3:45]>CCO.CCN(CC)CC>[Br-:1].[CH2:11]([N+:10]([CH2:44][CH3:45])([CH2:15][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:11][CH2:12][C:13]([C:16]2[CH:40]=[CH:39][C:19]3[N:20]=[C:21]([O:23][CH:24]4[CH2:29][CH2:28][N:27]([C:30]5[N:35]=[CH:34][C:33]([CH2:36][CH2:37][CH3:38])=[CH:32][N:31]=5)[CH2:26][CH2:25]4)[S:22][C:18]=3[CH:17]=2)=[CH:14][CH2:15]1)(=[O:9])=[O:8])[CH3:12]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 67468773HCID 67468773, compound

Product 1

HCID 54596658HCID 54596658, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-(1-(5-bromopentylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole (Example 30C, 22.8 mg, 0.035 mmol) in EtOH (1.5 mL) and Et3N (0.75 mL) was heated in microwave at 120° C. for 40 min. It was cooled to rt, Et2O (2 mL) was added. The solid was collected via filtering. The solid was dissolved in hot EtOH (0.5 mL), the vial was sealed and slowly cooled to rt. The precipitate was collected via filtering to afford the desired product as a white solid (15 mg, 51% yield). LCMS (m/z)=669 (M+H)+.

Workup

  1. temperatureIt was cooled to rt
  2. customThe solid was collected
  3. filtrationvia filtering
  4. dissolutionThe solid was dissolved in hot EtOH (0.5 mL)
  5. customthe vial was sealed
  6. temperatureslowly cooled to rt
  7. customThe precipitate was collected
  8. filtrationvia filtering

Sources & evidence

ORD record
ord-65df8d71905e489c8c33bfbb665a836f
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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