Sodium Hydroxide → HCID 72188386, compound

HRID 881720Notes

Reaction equation

HRID 881720 reaction equation
[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34]C)=[O:33])([CH2:27][CH2:28]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[N:15][CH:16]=3)=[N:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1>[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:28][CH2:27][C:26]([CH2:31][C:32]([OH:34])=[O:33])([CH2:29][CH2:30]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[N:15][CH:16]=3)=[N:7][N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86700828HCID 86700828, compound

Product 1

HCID 72188386HCID 72188386, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-(4-(4-(5-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (38 mg, 0.08 mmol) and THF (1 ml) was added NaOH (0.24 ml, 0.24 mmol). The mixture was stirred at room temperature for 7 hour. The resulting content was concentrated and purified on prep-HPLC to afford the title compound as white solid after drying (15 mg, 41% yield). HR/MS (M+H)+ found 461.2188. calc. 461.2184. RT: 5.63 (Condition Z). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85-2.13 (m, 10H) 2.27-2.40 (m, 6H) 3.69 (quind, J=8.43, 8.43, 8.43, 8.43, 0.88 Hz, 1H) 3.91 (s, 2H) 7.41 (d, J=8.59 Hz, 2H) 7.90-8.01 (m, 3H) 8.10 (dd, J=8.59, 2.78 Hz, 1H) 8.75 (d, J=3.03 Hz, 1H)

Workup

  1. concentrationThe resulting content was concentrated
  2. custompurified on prep-HPLC

Sources & evidence

ORD record
ord-18b2b4e30c194bb5b37259e6cd2062a7
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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