Ammonia → Ammonia

HRID 2278787Notes

Reaction equation

HRID 2278787 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:25][C@@H:26]5[CH2:28][O:27]5)=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:33]>CO>[NH3:7].[NH2:33][CH2:28][C@H:26]([OH:27])[CH2:25][O:24][C:20]1[C:21]([CH3:23])=[CH:22][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[C:8]([O:31][CH3:32])[N:7]=[C:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:11]=3)[O:16][N:15]=2)=[CH:18][C:19]=1[CH2:29][CH3:30]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86702019(S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole

Product 2

HCID 222AmmoniaHCID 70558998(S)-1-amino-3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole (350 mg, 0.804 mmol) in 7 N NH3 in methanol (15 mL) is stirred at 45° C. for 18 h. The solvent is evaporated and the crude product is purified by CC on silica gel eluting with DCM:7 N NH3 in methanol 94:6 to give (S)-1-amino-3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propan-2-ol (256 mg) as a pale yellow solid; LC-MS: tR=0.83 min, [M+H]+=453.22.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified by CC on silica gel eluting with DCM

Sources & evidence

ORD record
ord-dfaeffc775c044c88fbe29b450c73850
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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