Ammonia → HCID 66637119, compound

HRID 1094307Notes

Reaction equation

HRID 1094307 reaction equation
[OH:1][CH:2]([CH2:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]2[O:19][C:20]([C:23]3[S:24][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=3)=[N:21][N:22]=2)=[CH:13][C:12]=1[CH3:32])[CH2:3]OS(C)(=O)=O.[NH3:33]>C1COCC1.CO>[NH2:33][CH2:3][CH:2]([OH:1])[CH2:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]2[O:19][C:20]([C:23]3[S:24][C:25]([CH2:28][CH:29]([CH3:30])[CH3:31])=[CH:26][CH:27]=3)=[N:21][N:22]=2)=[CH:13][C:12]=1[CH3:32]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86639350HCID 86639350, compound

Product 1

HCID 66637119HCID 66637119, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methanesulfonic acid 2-hydroxy-3-{4-[5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propyl ester (220 mg, 0.458 mmol) in THF (10 mL) and 7 N NH3 in methanol (10 mL) is stirred at 65° C. for 15 h. The solvent is evaporated and the residue is separated by chromatography on prep. TLC plates with DCM containing 6% of 7 N NH3 in methanol to give 1-amino-3-{4-[5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (110 mg) as a yellow oil; LC-MS: tR=0.83 min, [M+1]+=402.48.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is separated by chromatography on prep

Sources & evidence

ORD record
ord-7f779e16b99e4ffcaf1133465d813380
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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