Phenol → HCID 69666432, compound

HRID 1839101Notes

Reaction equation

HRID 1839101 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH:15]([CH2:18][CH3:19])CO)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O>[O:26]([CH2:27][CH2:19][CH2:18][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21936606HCID 21936606, compound

Product 1

HCID 69666432HCID 69666432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)-2-ethylethanol (50 mg, 0.195 mmol) and N,N-dimethylformamide (2 mL) were combined. Phenol (37 mg, 0.390 mmol) and triphenylphosphine (102 mg) were added followed by diethyl azodicarboxylate (67 mg, 0.390 mmol). The resulting solution was sonicated for 1 hour. Analysis by LC-MS showed product and a small amount of starting material. The solvent was removed and the residue was purified by semi-preparative HPLC using Method A. Mass Measurement: TM=332, NM[M+H]+1=333.

Workup

  1. customThe resulting solution was sonicated for 1 hour
  2. customThe solvent was removed
  3. customthe residue was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-9b48516a66124e988ef0c57d1e62ab85
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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