Triethylamine → HCID 67239447, compound

HRID 2063204Notes

Reaction equation

HRID 2063204 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:15][C:16]1[C:17]([NH:21][C:22](=[O:24])[CH3:23])=[N:18][O:19][N:20]=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>ClC(Cl)C.CN(C1C=CN=CC=1)C>[C:22]([NH:21][C:17]1[C:16]([NH:15][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:10][C:2]=2[Cl:1])=[N:20][O:19][N:18]=1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 536687Furazanamine, 4-(acetylamino)-HCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

Product 1

HCID 67239447HCID 67239447, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

173 mg (0.5 mmol) of 2-chloro-4-(methylsulfonyl)benzoic acid and 191 mg (0.505 mmol) of N-(4-amino-1,2,5-oxadiazol-3-yl)acetamide are dissolved in 5 ml of dichloroethane at RT and treated with 0.071 ml (0.5 mmol) of triethylamine, 31 mg (0.25 mmol) of DMAP and 483 mg (0.76 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 24 h at RT and subsequently filtered through a glass frit. The residue is washed twice using in each case 1 ml of CH2Cl2. The filtrate is passed over a silica-gel-filled SPE cartridge and eluted twice using in each case 5 ml of a mixture of ethyl acetate/methyl tert-butyl ester (1:1). The organic phase is dried over Na2SO4 and evaporated. The residue is purified by preparative HPLC using acetonitrile/water. Yield 16 mg (9%).

Workup

  1. filtrationsubsequently filtered through a glass frit
  2. washThe residue is washed twice
  3. additiongel-filled SPE cartridge
  4. washeluted twice
  5. dry with materialThe organic phase is dried over Na2SO4
  6. customevaporated
  7. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-5f93d84652ca4fbf8628a74b4b6561a3
Source dataset
uspto-grants-2012_10
Patent number
US08288316B2

Reaction notes

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