Hydrochloric Acid → HCID 59464318, compound

HRID 1713759Notes

Reaction equation

HRID 1713759 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:19][CH:18]=2)=[O:15])=[N:11][N:10]=1.CO.[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:19][CH:18]=2)=[O:15])=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59464153HCID 59464153, compound

Product 1

HCID 59464318HCID 59464318, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}butanoate (Example 483) (174 mg, 0.44 mmol) was stirred in THF: MeOH (8 mL of a 1:1 mixture) and NaOH (2.5 mL of 2M aqueous solution) was added. The mixture was stirred for 8.5 h then acidified (2M HCl), allowed to stand overnight, then concentrated in vacuo. The precipitate was filtered and washed with water and then Et2O to give the title compound (94 mg, 56%) as a solid; 1H NMR δ 1.77-1.84 (2H, m), 2.22 (2H, t), 2.59 (2H, t), 7.14-7.21 (3H, m), 7.25-7.34 (2H, m), 7.70-7.72 (2H, m), 8.02-8.07 (1H, m), 10.74 (1H, s), 10.94 (1H, s), 11.98 (1H, s); MS m/e MH+ 385.

Workup

  1. waitto stand overnight
  2. concentrationconcentrated in vacuo
  3. filtrationThe precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-82dc2056464540a587a3dfc7911d8151
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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