Ethyl Acetate → HCID 57500715, compound

HRID 1920036Notes

Reaction equation

HRID 1920036 reaction equation
[Si]([O:18][CH2:19][C:20]([CH3:53])([CH3:52])[CH2:21][NH:22][C@@H:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[N:36][C:37]=3[C:47]3[CH:48]=[N:49][NH:50][CH:51]=3)[N:32]=2)=[CH:27][CH:26]=1)[CH3:24])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[CH3:53][C:20]([CH3:52])([CH2:21][NH:22][C@@H:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:40]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[N:36][C:37]=3[C:47]3[CH:48]=[N:49][NH:50][CH:51]=3)[N:32]=2)=[CH:27][CH:26]=1)[CH3:24])[CH2:19][OH:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57500735HCID 57500735, compound

Product 1

HCID 57500715HCID 57500715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-{[teri-butyl(diphenyl)silyl]oxy}-2,2-dimethyl-N-[(1R)-1-{4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]phenyl}ethyl]propan-1-amine (2-5, 0.050 g, 0.070 mmol) in THF (1.0 mL) was added 1M tetrabutylammonium fluoride in THF (0.70 mL, 0.70 mmol) at room temperature and the reaction was stirred at room temperature for 15 hours. The reaction was poured into ethyl acetate, washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under vacuum. Purification by reverse phase chromatography (5-95% acetonitrile/water/0.1% TFA; Water Sunfire C18) gave (2,2-dimethyl-3-{[(1R)-1-{4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]phenyl}ethyl]amino}propan-1-ol (2-6) as a yellow solid. HRMS (M+H)+: calculated 478.2602; found 478.2626.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by reverse phase chromatography (5-95% acetonitrile/water/0.1% TFA; Water Sunfire C18)

Sources & evidence

ORD record
ord-ae2724c3b7174b0787c6f57b7830f8e1
Source dataset
uspto-grants-2012_05
Patent number
US08168652B2

Reaction notes

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