Triethylamine → HCID 67041950, compound

HRID 2063202Notes

Reaction equation

HRID 2063202 reaction equation
C([C:9]1[C:10]([NH:14][C:15](=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([CH2:26][O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[C:17]=2[Cl:33])=[N:11][O:12][N:13]=1)(=O)C1C=CC=CC=1.ClC1C(COCC(F)(F)F)=C(S(C)(=O)=O)C=CC=1[C:38](O)=[O:39].NC1C(C(C2C=CC=CC=2)=O)=NON=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>ClCCl.CN(C1C=CN=CC=1)C>[Cl:33][C:17]1[C:18]([CH2:26][O:27][CH2:28][C:29]([F:31])([F:30])[F:32])=[C:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:20]=[CH:21][C:16]=1[C:15]([NH:14][C:10]1[C:9]([O:39][CH3:38])=[N:13][O:12][N:11]=1)=[O:34]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1423314-Benzoyl-3-furazanamineHCID 151328952-Chloro-4-methylsulfonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoic acidHCID 67041595HCID 67041595, compound

Product 1

HCID 67041950HCID 67041950, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Synthesis of N-(4-benzoyl-1,2,5-oxadiazol-3-yl)-2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide (example No. 11-5 in the tables) 204 mg (0.59 mmol) of 2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]-benzoic acid and 111 mg (0.59 mmol) of (4-amino-1,2,5-oxadiazol-3-yl)(phenyl)-methanone are dissolved in 10 ml of dichloromethane at RT and treated with 59 mg (0.599 mmol) of triethylamine, 14 mg (0.19 mmol) of DMAP and 561 mg (0.882 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF). The reaction mixture is stirred for 30 h at RT and subsequently washed twice with in each case 5 ml of water. The organic phase is dried over Na2SO4 and evaporated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 50 mg (15%).

Workup

  1. washsubsequently washed twice with in each case 5 ml of water
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated
  4. customThe residue is purified by column chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a29cee5046a644d6ad4950795a0ad2bc
Source dataset
uspto-grants-2012_10
Patent number
US08288316B2

Reaction notes

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