Tetrabutylammonium Fluoride → HCID 10250607, compound

HRID 1178434Notes

Reaction equation

HRID 1178434 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH2:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH:32]([NH:40][C:41]([C:43]2[NH:47][C:46]3[S:48][C:49]([Cl:51])=[CH:50][C:45]=3[CH:44]=2)=[O:42])[C:31]1=[O:52])(C(C)(C)C)(C)C>C1COCC1>[Cl:51][C:49]1[S:48][C:46]2[NH:47][C:43]([C:41]([NH:40][CH:32]3[CH2:33][C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:30]([CH2:29][CH2:28][CH2:27][OH:26])[C:31]3=[O:52])=[O:42])=[CH:44][C:45]=2[CH:50]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21906851N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 10250607HCID 10250607, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.0 M in THF, 4.92 mL, 4.92 mmol) was added to N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 20, 1.84 g, 3.56 mmol) in THF (15 mL) and the reaction was stirred for 48 hours. The reaction was quenched by the addition of EtOAc (50 mL) and NH4Cl (aq.) (20 mL) and the organic layer was dried (MgSO4), filtered and evaporated. Purification by column chromatography afforded the title compound (1.24 g, 3.08 mmol, 86%) as a white solid.

Workup

  1. customThe reaction was quenched by the addition of EtOAc (50 mL) and NH4Cl (aq.) (20 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-03a36a4ef2e843fdaa96ef02130f47f7
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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