Tetrabutylammonium Fluoride → HCID 58204294, compound

HRID 886271Notes

Reaction equation

HRID 886271 reaction equation
[Si]([O:8][C:9]([CH3:40])([CH3:39])[CH2:10][N:11]1[CH:15]=[C:14]([C:16]2[CH:37]=[CH:36][C:19]3[C:20]4[N:21]([CH:25]=[C:26]([C:28]5[N:32]([CH:33]([CH3:35])[CH3:34])[N:31]=[CH:30][N:29]=5)[N:27]=4)[CH2:22][CH2:23][O:24][C:18]=3[CH:17]=2)[N:13]=[C:12]1[CH3:38])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:33]([N:32]1[C:28]([C:26]2[N:27]=[C:20]3[C:19]4[CH:36]=[CH:37][C:16]([C:14]5[N:13]=[C:12]([CH3:38])[N:11]([CH2:10][C:9]([CH3:40])([OH:8])[CH3:39])[CH:15]=5)=[CH:17][C:18]=4[O:24][CH2:23][CH2:22][N:21]3[CH:25]=2)=[N:29][CH:30]=[N:31]1)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 670506769-(1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-1H-imidazol-4-yl)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 58204294HCID 58204294, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-(1-(2-(tert-Butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-1H-imidazol-4-yl)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (110 mg, 0.196 mmol) was dissolved in 5 mL of THF, tetrabutylammonium fluoride (TBAF, 102 mg, 0.392 mmol) was added at 0° C. The temperature was allowed to warm up to room temperature slowly and stirred at room temperature for over night. Concentrated, the residue was portioned with EtOAc-water to give 30 mg of 265. Yield=36%. 1H NMR (CDCl3, 400 MHz): δ8.48 (d, J=8.0 Hz, 1H), 7.87 (s, 1H), 7.64 (s, 1H), 7.51-7.47 (m, 2H), 7.26 (s, 1H), 6.03-5.99 (m, 1H), 4.51-4.43 (m, 4H), 3.85 (s, 1H), 2.47 (s, 3H), 1.65-1.56 (m, 6H), 1.28-1.26 (m, 6H). LC-MS: m/z=433 [M+H+]

Workup

  1. concentrationConcentrated

Sources & evidence

ORD record
ord-87404156b7274c42a363b1f253268d41
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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