Hydrochloric Acid → HCID 44548736, compound

HRID 1512918Notes

Reaction equation

HRID 1512918 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][NH:28][C@@H:29]([C:31]([O-:33])=[O:32])[CH3:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][NH:28][C@@H:29]([C:31]([OH:33])=[O:32])[CH3:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86637987HCID 86637987, compound

Product 1

HCID 44548736HCID 44548736, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-D-alaninate (D80) (110 mg) in THF (2 mL) was added aqueous NaOH (2 M, 2 mL). The reaction was stirred at room temperature overnight. The reaction mixture was acidified with HCl (2 M) to pH 6-7. The resulting solid was separated and suspended in methanol (2 mL) with stirring, HCl (2M) was added until the solid dissolved completely. The solution was freeze dried to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-D-alanine (E59) (60 mg, HCl salt). δH (DMSO-d6, 400 MHz): 1.35 (6H, d), 1.48 (3H, d), 3.71 (3H, s), 3.86 (1H, q), 4.35 (2H, s), 4.89 (1H, m), 7.28 (1H, t), 7.45 (1H, d), 7.51 (1H, d), 7.60 (1H, s), 8.03 (1H, d), 8.13 (1H, d), 8.20 (1H, s). MS (ES): C24H26ClN4O4 requires 468; found 380.1 (M—C3H6NO2+).

Workup

  1. customThe resulting solid was separated
  2. stirringwith stirring
  3. additionHCl (2M) was added until the solid
  4. dissolutiondissolved completely
  5. customdried

Sources & evidence

ORD record
ord-c54a7016cd644b0d99dce93dd4e3154c
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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