Ammonia → 1-Amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethylphenoxy}-propan-2-ol

HRID 1676144Notes

Reaction equation

HRID 1676144 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:29])=[C:7]([C:10]2[O:14][C:13]([C:15]3[CH:26]=[C:25]([CH3:27])[C:18]([O:19][CH2:20][CH:21]([OH:24])[CH2:22]O)=[C:17]([CH3:28])[CH:16]=3)=[N:12][N:11]=2)[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].CC[N:32](CC)CC.CS(Cl)(=O)=O.N>C1COCC1.CO>[NH2:32][CH2:22][CH:21]([OH:24])[CH2:20][O:19][C:18]1[C:25]([CH3:27])=[CH:26][C:15]([C:13]2[O:14][C:10]([C:7]3[S:8][CH:9]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]=3[CH3:29])=[N:11][N:12]=2)=[CH:16][C:17]=1[CH3:28]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 237292443-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

Product 1

HCID 594978831-Amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethylphenoxy}-propan-2-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol (90 mg, 0.22 mmol) in THF (4 mL) are added NEt3 (0.14 mL) and, subsequently, methanesulfonlychloride (0.02 mL, 0.26 mmol). The mixture is stirred at rt for 3 h. A solution of NH3 in MeOH (7M, 4 mL) is added and the mixture is heated at 60° C. for 15 h. The mixture is evaporated, 1M aq. NaOH (3 mL) is added and the mixture is extracted with EA (2×20 mL). The organic extracts are dried (Na2SO4), filtered and evaporated to give crude 1-amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethylphenoxy}-propan-2-ol; LC-MS: tR=0.86 min, [M+1]+=416.32.

Workup

  1. temperaturethe mixture is heated at 60° C. for 15 h
  2. customThe mixture is evaporated
  3. addition1M aq. NaOH (3 mL) is added
  4. extractionthe mixture is extracted with EA (2×20 mL)
  5. dry with materialThe organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-70fc6cd5e2a44731804f76b15940a1a4
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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