Dimethylformamide → 3-Methoxypropyl 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine-1-carboxylate

HRID 2090595Notes

Reaction equation

HRID 2090595 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].C(N1C=CN=C1)(N1C=CN=C1)=O.Br.[CH3:20][C:21]1([CH3:44])[CH2:30][CH2:29][C:28]([CH3:32])([CH3:31])[C:27]2[CH:26]=[C:25]([C:33]3[N:34]=[C:35]([CH:38]4[CH2:43]CNC[CH2:39]4)[S:36][CH:37]=3)[CH:24]=[CH:23][C:22]1=2.[CH3:45][N:46]([CH:48]=[O:49])[CH3:47]>>[CH3:20][C:21]1([CH3:44])[CH2:30][CH2:29][C:28]([CH3:31])([CH3:32])[C:27]2[CH:26]=[C:25]([C:33]3[N:34]=[C:35]([CH:38]4[CH2:39][CH2:47][N:46]([C:48]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:49])[CH2:45][CH2:43]4)[S:36][CH:37]=3)[CH:24]=[CH:23][C:22]1=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 741163-Methoxy-1-propanolHCID 671662304-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide

Product 1

HCID 582464933-Methoxypropyl 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine-1-carboxylate

Procedure

41 μl (0.42 mmol) of 3-methoxy-1-propanol are dissolved in 3 ml of DMF, 69 mg (0.42 mmol) of 1,1′-carbonyldiimidazole are added, and the mixture is stirred at room temperature for 2 h. 122 mg (0.28 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]-piperidine hydrobromide are subsequently added, and the reaction mixture is stirred at room temperature for 3 days. The reaction mixture is evaporated, the residue is taken up in ethyl acetate and washed with 1 N HCl, saturated sodium hydrogencarbonate solution and saturated sodium chloride solution. The crude mixture is purified by column chromatography on silica gel. Yield: 90 mg of “A46”, ESI: 471 (M+H), HPLC: 4.20 min.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 3 days
  2. customThe reaction mixture is evaporated
  3. washwashed with 1 N HCl, saturated sodium hydrogencarbonate solution and saturated sodium chloride solution
  4. customThe crude mixture is purified by column chromatography on silica gel
  5. custom4.20 min.

Sources & evidence

ORD record
ord-1e84699702e54e108643216a8bdf9a4a
Source dataset
uspto-grants-2013_05
Patent number
US08436186B2

Reaction notes

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