Sodium Hydroxide → HCID 59464220, compound

HRID 1713780Notes

Reaction equation

HRID 1713780 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[O:18][C:17]([C:19]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:33][CH2:32][CH:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]5)=[N:26][CH:27]=4)=[O:20])=[N:16][N:15]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[O:18][C:17]([C:19]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:33][CH2:32][CH:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]5)=[N:26][CH:27]=4)=[O:20])=[N:16][N:15]=3)=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59464209HCID 59464209, compound

Product 1

HCID 59464220HCID 59464220, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 1-(5-{[(5-{[4-(4-chlorophenoxy)phenyl]amino}-1,3,4-oxadiazol-2-yl)carbonyl]amino}pyridin-2-yl)piperidine-4-carboxylate (Example 638; 340 mg, 0.62 mmol) in MeOH (5 mL) was added 2M NaOH (1.5 mL, 3.10 mmol) and the reaction mixture was allowed to stir at ambient temperature overnight. The solvent was evaporated and the aqueous residue adjusted to pH ˜1-2 with 2M HCl, the solid was filtered and dried to give the title compound (284 mg, 0.531 mmol, 86%); 1H NMR δ 1.79-1.90 (m, 2H), 2.14-2.19 (m, 2H), 2.78-2.84 (m, 1H), 3.33-3.40 (m, 2H), 4.35-4.39 (m, 2H), 7.23 (d, 2H), 7.37 (d, 2H), 7.43 (d, 1H), 7.64 (d, 2H), 7.88 (d, 2H), 8.33 (d, 1H), 8.73 (s, 1H), 11.26 (s, 1H), 11.36 (s, 1H); CO2H not seen; MS m/e MH+ 535.

Workup

  1. customThe solvent was evaporated
  2. filtrationthe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-3bb298df39484ca581737b6c1fb21d9e
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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