Tetrabutylammonium Fluoride → HCID 57526834, compound

HRID 1452632Notes

Reaction equation

HRID 1452632 reaction equation
[C:1]([O:5][C:6]([N:8]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH3:51])=[CH:45][CH:44]=1)[C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)[C:10]=1[CH2:32][CH2:33][CH2:34][O:35][Si](C(C)(C)C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:43]1[CH:44]=[CH:45][C:46]([O:49][CH2:50][CH3:51])=[CH:47][CH:48]=1)[C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:20]2)[C:10]=1[CH2:32][CH2:33][CH2:34][OH:35])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69508739HCID 69508739, compound

Product 1

HCID 57526834HCID 57526834, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (1.3 mL) solution containing tert-butyl (S)-3-[7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-6-(3-tert-butyldimethylsiloxypropyl)pyrazolo[1,5-a]pyrimidin-5-ylamino]piperidine-1-carboxylate (13.3 mg), was added tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 26 μL), and the mixture was stirred at room temperature for 3 hr. After the reaction, the mixture was purified with PTLC (50% ethyl acetate-hexane) to obtain the title compound (7.7 mg).

Workup

  1. customAfter the reaction
  2. customthe mixture was purified with PTLC (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b29cf0b7ab4543a08510032261c8d1de
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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