Triethylamine → HCID 68327817, compound

HRID 511739Notes

Reaction equation

HRID 511739 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[C:9]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:22]([C:29]1[O:33][C:32]([NH2:34])=[N:31][N:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:22]([C:29]1[O:33][C:32]([NH:34][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:10]([CH2:11][O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:2]=2[Cl:1])=[N:31][N:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27566345-benzyl-1,3,4-oxadiazol-2-amineHCID 151328952-Chloro-4-methylsulfonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoic acid

Product 1

HCID 68327817HCID 68327817, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

90 mg (0.26 mmol) of 2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoic acid and 45 mg (0.26 mmol) of 5-benzyl-1,3,4-oxadiazol-2-amine are dissolved at room temperature (RT) in 8 ml of CH2Cl2. Then 248 mg (0.398 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added, the mixture is stirred at RT for one hour and then 0.181 ml (1.3 mmol) of triethylamine, 6 mg (0.052 mmol) of 4-dimethylaminopyridine are added. Then the mixture is stirred at RT for 20 h and washed twice with 4 ml each time of water, dried over Na2SO4 and concentrated. The residue is purified by column chromatography (prep. HPLC; acetonitrile/water). Yield 70 mg (45%).

Workup

  1. stirringThen the mixture is stirred at RT for 20 h
  2. washwashed twice with 4 ml each time of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography (prep. HPLC; acetonitrile/water)

Sources & evidence

ORD record
ord-164dccc0caf843f6a6219e9323760166
Source dataset
uspto-grants-2015_08
Patent number
US09101141B2

Reaction notes

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