Diisopropylethylamine → HCID 86719164, compound

HRID 2172695Notes

Reaction equation

HRID 2172695 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:4]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:55]([N:62]([CH3:66])[CH2:63][CH2:64][NH2:65])([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56]>C(Cl)Cl>[CH3:66][N:62]([CH2:63][CH2:64][NH:65][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([C:5]2[N:4]=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=2)=[CH:16][CH:15]=1)[C:55](=[O:56])[O:57][C:58]([CH3:61])([CH3:59])[CH3:60]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2756424N-Boc-N-methylethylenediamineHCID 104914054-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate

Product 1

HCID 86719164HCID 86719164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (1 g, 3.87 mmol) in DCM (10 ml) was added COMU (1.825 g, 4.26 mmol) and DIPEA (0.812 ml, 4.65 mmol). The yellow solution was stirred for 2 min at rt and turned red. N-Boc-N-methyl-ethylenediamine (0.810 g, 4.65 mmol) was added and the reaction mixture was stirred at reflux for 1 hr, allowed to cool to rt and washed with water, saturated aqueous NH4Cl, and extracted with EtOAc. The organic layer was dried over Na2SO4 and the solvent was removed in vacuum. The final product was purified according to Method B in Examples 124-156 general method.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureat reflux for 1 hr
  3. temperatureto cool to rt
  4. washwashed with water, saturated aqueous NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customthe solvent was removed in vacuum
  8. customThe final product was purified

Sources & evidence

ORD record
ord-38e2b722836b46d7a4cabfc2d09a877e
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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