Formamidine acetate → HCID 58653692, compound

HRID 1676085Notes

Reaction equation

HRID 1676085 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[NH:4][CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[C:30](O)(=O)C.C(N)=N>C(OCCO)C>[C:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]([CH:5]([N:4]2[C:3]3[CH:23]=[CH:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][C:2]=3[N:1]=[CH:30]2)[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 58653655HCID 58653655, compound

Product 1

HCID 58653692HCID 58653692, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

To a solution of methyl 3-(2-amino-4-nitroanilino)-3-(1,1′-biphenyl)-4-ylpropanoate (60 mg, 153 μmol) in 2-ethoxyethanol (1 mL) was added formamidine acetate (48 mg, 461 μmol). The solution was heated to reflux for 6 hours, then cooled to room temperature, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=6.11 min, MH+ 402].

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 6 hours
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-614eccd64c2e489dad426441063d5495
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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