Tetrabutylammonium Fluoride → HCID 54589186, compound

HRID 571114Notes

Reaction equation

HRID 571114 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:39])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[O:32])[CH:25]=3)=[CH:15][CH:14]=2)[N:7]([C:40]2[CH:45]=[CH:44][C:43]([O:46][Si](C(C)C)(C(C)C)C(C)C)=[C:42]([Cl:57])[CH:41]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CO>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:39])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[O:32])[CH:25]=3)=[CH:15][CH:14]=2)[N:7]([C:40]2[CH:45]=[CH:44][C:43]([OH:46])=[C:42]([Cl:57])[CH:41]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67468081HCID 67468081, compound

Product 1

HCID 54589186HCID 54589186, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(4-(3-(3-tert-butyl-1-(3-chloro-4-(triisopropylsilyloxy)phenyl)-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)morpholine-4-carboxamide (70 mg, 0.078 mmol) in dry THF (2.0 mL) was added TBAF (1.0 M in THF, 116 μL, 0.116 mmol) and the reaction mixture kept at RT for 16 hr. The reaction mixture was diluted with MeOH (1.0 mL) and after 5 min was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 4 g, EtOAc in isohexane, 0-100%, gradient elution) to afford the title compound, Example 12, as a pink solid (20 mg, 39%); Rt 3.97 min (Method 1 basic); m/z 655 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.27 (9H, s), 3.36 (4H, m), 3.52 (4H, m), 6.37 (1H, s), 6.61 (1H, dd), 7.12 (1H, d), 7.31 (1H, d), 7.35 (1H, dd), 7.37 (1H, d), 7.54 (1H, d), 7.57 (1H, m), 7.64 (1H, m), 7.84 (1H, d), 7.91 (1H, br s), 8.06 (1H, d), 8.12 (1H, d), 8.74 (1H, s), 9.09 (1H, s), 9.26 (1H, s), 10.62 (1H, br s).

Workup

  1. customwas evaporated in vacuo
  2. customThe residue was purified by flash column chromatography (SiO2, 4 g, EtOAc in isohexane, 0-100%, gradient elution)

Sources & evidence

ORD record
ord-eba88a17f45941c295787dcf5c27291a
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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