Sodium Hydroxide → HCID 72188385, compound

HRID 881719Notes

Reaction equation

HRID 881719 reaction equation
[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34]C)=[O:33])([CH2:27][CH2:28]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:28][CH2:27][C:26]([CH2:31][C:32]([OH:34])=[O:33])([CH2:29][CH2:30]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86700827HCID 86700827, compound

Product 1

HCID 72188385HCID 72188385, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a reaction vial containing methyl 2-(4-(4-(5-(5-tert-butyl-1,3,4-oxadiazol-2-ylamino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (55 mg, 0.12 mmol) was added THF (1.5 ml) and a solution of 1N NaOH (0.35 ml, 0.35 mmol). The mixture was stirred vigorously at room temperature for overnight. The resulting mixture was concentrated to dryness and the residue was taken up in water. The mixture was acidified with 1N HCl to a pH of between 3 and 4 affording a thick residue. The residue was concentrated to dryness and taken up in MeOH to form fine slurry. The slurry was filtered and washed with small amount of MeOH and water to afford the title compound as white solid after drying (36 mg, 67% yield). HR/MS (M+H)+ found 463.2354. calc. 463.2345. RT: 5.76 (Condition Z). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (br. s, 1H) 10.78 (br. s, 1H) 8.76 (d, J=2.78 Hz, 1H) 8.04-8.13 (m, 1H) 7.90-8.01 (m, 3H) 7.41 (d, J=8.59 Hz, 2H) 3.90 (s, 2H) 2.29 (s, 2H) 1.82-2.08 (m, 8H) 1.36 (s, 9H)

Workup

  1. concentrationThe resulting mixture was concentrated to dryness
  2. customaffording a thick residue
  3. concentrationThe residue was concentrated to dryness
  4. customto form fine slurry
  5. filtrationThe slurry was filtered
  6. washwashed with small amount of MeOH and water

Sources & evidence

ORD record
ord-69b6bd1db74b42df8660619719ff2e99
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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