Triethylamine → HCID 178440817, compound

HRID 2042006Notes

Reaction equation

HRID 2042006 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:18])[C:15](O)=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH:29]1[C:33]([NH2:34])=[N:32][N:31]=[N:30]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:18])[C:15]([NH:34][C:33]2[NH:32][N:31]=[N:30][N:29]=2)=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59577113HCID 59577113, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178440817HCID 178440817, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of [4-(2-tert-butylphenoxy)piperidin-1-yl](oxo)acetic acid (300 mg, 0.98 mmol) obtained in Example 52 and oxalyl chloride (126 μL, 1.47 mmol) in toluene (5 ml) was stirred at room temperature for 3 hr. The reaction mixture was concentrated, and DMF (1 mL) was added to the residue. The mixture was added to a solution of 1H-tetrazole-5-amine (255 mg, 3.0 mmol) and triethylamine (205 μL, 1.47 mmol) in toluene (10 ml) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was partitioned between ethyl acetate-1N hydrochloric acid, and the ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (317 mg, 87%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDMF (1 mL) was added to the residue
  3. temperaturecooling
  4. customThe reaction mixture was partitioned between ethyl acetate-1N hydrochloric acid
  5. washthe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed6ed5552e58479aa79a68e4bfd9d6af
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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