Tetrabutylammonium Fluoride → HCID 59743545, compound

HRID 1947022Notes

Reaction equation

HRID 1947022 reaction equation
[Si]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]3[CH2:35][CH2:34][CH:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH2:32][CH2:31]3)[N:24]=2)[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]3[CH2:31][CH2:32][CH:33]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH2:34][CH2:35]3)[N:24]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69309770HCID 69309770, compound

Product 1

HCID 59743545HCID 59743545, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[4-(4-{4-[3-(t-butyl-dimethylsilanyloxy)-pyrrolidin-1-yl]-indol-1-yl}-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide (0.35 mmol) was mixed with TBAF (10 eq, 3.5 mL) in anhydrous THF (15 mL) and allowed to stir for 1.5 h at RT, and then heated to 68° C. The reaction mixture was washed with NH4Cl/H2O, extracted into EtOAc (6×15 mL), and further washed with H2O (6×30 mL). The product was isolated via chromatography (prep. TLC in NH4OH/MeOH/DCM) as N-[4-(4-{4-[3-(hydroxy)-pyrrolidin-1-yl]-indol-1-yl}-pyrimidin-2-yl-amino)-cyclohexyl]-methanesulfonamide (Compound 311, 35 mg).

Workup

  1. temperatureheated to 68° C
  2. washThe reaction mixture was washed with NH4Cl/H2O
  3. extractionextracted into EtOAc (6×15 mL)
  4. washfurther washed with H2O (6×30 mL)

Sources & evidence

ORD record
ord-8c81c49b33c24b34a2729a9f722ff692
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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