Ammonia → HCID 59497867, compound

HRID 1676139Notes

Reaction equation

HRID 1676139 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[C:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:23]=3[CH3:24])[O:16][N:15]=2)[CH:5]=[C:6]([CH3:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.C1COCC1.[NH3:34]>CO.[OH-].[Na+]>[NH2:34][CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[C:22]([CH2:25][CH:26]([CH3:27])[CH3:28])[C:23]=3[CH3:24])[O:16][N:15]=2)=[CH:5][C:6]=1[CH3:13]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 87367383HCID 87367383, compound

Product 1

HCID 59497867HCID 59497867, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of rac-3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,2,4]oxadiazole (382 mg, 0.959 mmol) in 7 N NH3 in MeOH (10 mL) and THF (5 mL) is stirred at 60° C. for 15 h. The mixture is diluted with 1M aq. NaOH (30 mL) and extracted with DCM (4×75 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to give rac-1-amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (419 mg) as a pale yellow solid; LC-MS: tR=0.90 min, [M+1]=416.42.

Workup

  1. extractionextracted with DCM (4×75 mL)
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5d55e977a21a447592a17bfc4ac9abef
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

Loading…