Diisopropylethylamine → Benzyl 2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881740Notes

Reaction equation

HRID 881740 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[C:33](N1C=CC=CC1=O)(N1C=CC=CC1=O)=S.[NH2:49][CH2:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:52]([C:51]1[O:56][C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[CH:10][C:11]([C:14]45[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25][CH2:26][C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=6)=[O:24])([CH2:18][CH2:19]4)[O:16][CH2:15]5)=[CH:12][CH:13]=3)=[N:6][CH:7]=2)=[N:49][CH:50]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 4266281-Amino-3,3-dimethylbutan-2-oneHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86700842Benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Product 1

HCID 86700843Benzyl 2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (150 mg, 0.350 mmol) in DCM (6 ml) at room temperature was added 1,1′-thiocarbonyldi-2(1H)-pyridone (85 mg, 0.368 mmol) and the reaction was stirred at room temperature for 0.5 hr. To the mixture was added 1-amino-3,3-dimethylbutan-2-one (80 mg, 0.525 mmol) and DIPEA (0.110 ml, 0.630 mmol) and the mixture was stirred at 40° C. or until the reaction was completed. To the mixture was added EDC.HCl (268 mg, 1.400 mmol) and the reaction was stirred at 40° C. overnight. The reaction mixture was concentrated and purified by flash chromatography (10 to 50% EtOAc/Heptane) to give the title compound (100 mg, 51.8% yield). LC/MS, ESI-MS(+) m/z 552.1, RT: 1.73 (Condition R).

Workup

  1. stirringthe mixture was stirred at 40° C. or until the reaction
  2. stirringthe reaction was stirred at 40° C. overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by flash chromatography (10 to 50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-9e9b657c7480446086a9395fced475f1
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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