HCID 68554551, compound → HCID 135964215, compound

HRID 2040826Notes

Reaction equation

HRID 2040826 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[S:20][C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH:28]([CH3:30])[CH3:29])[CH:22]=3)=[N:18][N:17]=2)=[CH:11][C:10]=1[CH2:31][CH3:32])C1C=CC=CC=1>CC(=O)OCC.C(O)(=O)C>[CH2:31]([C:10]1[CH:11]=[C:12]([C:16]2[S:20][C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH:28]([CH3:29])[CH3:30])[CH:22]=3)=[N:18][N:17]=2)[CH:13]=[C:14]([CH3:15])[C:9]=1[OH:8])[CH3:32]

Participants

4

Reactant 1

HCID 68554551HCID 68554551, compound

Product 1

HCID 135964215HCID 135964215, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]thiadiazol-2-yl]-2-isopropyl-6-methyl-pyridine (837 mg, 1.88 mmol) in EA (30 mL) 33% HBr in acetic acid (1 mL) is added. The mixture is stirred at rt for 3 h before it is diluted with EA, washed twice with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 2-ethyl-4-[5-(2-isopropyl-6-methyl-pyridin-4-yl)-[1,3,4]thiadiazol-2-yl]-6-methyl-Phenol (540 mg) as a pale yellow oil; LC-MS: tR=0.92* min, [M+1]+=354.14.

Workup

  1. washwashed twice with sat. aq. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-f5531dcb76d24e2e81371433fed749ed
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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