Tetrabutylammonium Fluoride → (E)-N-(2-Hydroxyethyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzenesulfonamide

HRID 1772664Notes

Reaction equation

HRID 1772664 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]3[CH:27]=[C:28](/[CH:30]=[CH:31]/[C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:29]=[C:25]3[C:24]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)=[N:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]3[CH:27]=[C:28](/[CH:30]=[CH:31]/[C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:29]=[C:25]3[C:24]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)=[N:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734677(E)-N-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzenesulfonamide

Product 1

HCID 86345646(E)-N-(2-Hydroxyethyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 33a (135 mg, 0.201 mmol) in THF (5 mL), TBAF (112 mg, 0.402 mmol) was added. The resulting mixture was stirred at rt for 2 h and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexanes, 0-100%). The solid obtained was suspended in 50% diethyl ether/hexanes, sonicated, and collected by filtration to obtain the title compound 73. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 7.48-7.52 (m, 2H), 7.06-7.13 (m, 6H), 6.99-7.04 (m, 2H), 6.87-6.92 (m, 1H), 6.78-6.84 (m, 1H), 6.67-6.73 (m, 2H), 3.90-3.95 (m, 1H), 3.44-3.50 (m, 4H), 2.94-2.99 (m, 4H), 2.54-2.61 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H28N6O4S: 557.2 (M+H). Found 557.2.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexanes, 0-100%)
  3. customThe solid obtained
  4. customsonicated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1274951018cc459fa5131ca488a458b9
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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