Tetrabutylammonium Fluoride → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712267Notes

Reaction equation

HRID 712267 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:17]=[N:18][N:19]([CH2:21][Si](C)(C)C)[CH:20]=3)=[CH:14][C:13]([C:26]3[CH:27]=[N:28][C:29]([N:32]4[CH2:37][CH2:36][C:35]([CH3:43])([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]4)=[N:30][CH:31]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:17]=[N:18][N:19]([CH3:21])[CH:20]=3)=[CH:14][C:13]([C:26]3[CH:31]=[N:30][C:29]([N:32]4[CH2:37][CH2:36][C:35]([CH3:43])([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]4)=[N:28][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 86663978Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[1-(trimethylsilylmethyl)triazol-4-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 86663979Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[1-(trimethylsilylmethyl)triazol-4-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (95 mg, 0.1529 mmol) in 1 mL of THF was cooled to 0° C. Water (5 drops) was added followed by tetra butyl ammonium fluoride (0.153 mL, 1.0 M solution in THF). The reaction was stirred at rt for 18 hours, another 0.2 mL of tetra butyl ammonium fluoride solution added and stirred for another 24 hours. The reaction was filtered through a pad of keiselguhr and the solvent removed under vacuum to yield a brown gum. The crude material was purified by preperative HPLC to give the product as a brown gum 63 mg, 75% yield.

Workup

  1. stirringstirred for another 24 hours
  2. filtrationThe reaction was filtered through a pad of keiselguhr
  3. customthe solvent removed under vacuum
  4. customto yield a brown gum
  5. customThe crude material was purified by preperative HPLC

Sources & evidence

ORD record
ord-3d5e3b4652654b72b37153f9a1153a0c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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