Triphenylphosphine → HCID 68972752, compound

HRID 2203564Notes

Reaction equation

HRID 2203564 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([OH:17])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1.C(OC1C=C(C=CC=1)N)C1C=CC=CC=1.COCCC(Cl)=O.C(OC1C=CC(N)=CC=1)C1C=CC=CC=1.C(OCC(Cl)=O)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:100]1[CH2:105][CH2:104][N:103]([C:106]([O:108][C:109]([CH3:112])([CH3:111])[CH3:110])=[O:107])[CH2:102][CH2:101]1>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH:100]4[CH2:105][CH2:104][N:103]([C:106]([O:108][C:109]([CH3:112])([CH3:111])[CH3:110])=[O:107])[CH2:102][CH2:101]4)=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1

Participants

10

Reactant 8

HCID 11776TriphenylphosphineHCID 228604-BenzyloxyanilineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 84189Ethoxyacetyl chlorideHCID 928923-BenzyloxyanilineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27597283-Methoxypropanoyl chlorideHCID 136347851HCID 136347851, compound2×

Product 1

HCID 68972752HCID 68972752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A modification on the methods described in Parts A-H of Example 2 were used to prepare 2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol, with 3-benzyloxyaniline and 3-methoxypropanoyl chloride used in lieu of 4-benzyloxyaniline and ethoxyacetyl chloride, respectively. A solution of diisopropyl azodicarboxylate (6.28 mL, 31.9 mmol) in tetrahydrofuran (25.5 mL) was added dropwise to a mixture of 2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol (7.28 g, 25.5 mmol), triphenylphosphine (8.36 g, 31.9 mmol), and t-butyl 4-hydroxypiperidine-1-carboxylate (6.42 g, 31.9 mmol) in tetrahydrofuran (191 mL) at 5° C. The mixture was allowed to warm to room temperature. After 2 days, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, gradient elution with 1.5-4% methanol in dichloromethane) to yield 9.77 g of tert-butyl 4-{[2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxylate as a gray amorphous solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, gradient elution with 1.5-4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-dd8191300b2549598ee38d2ec69122b3
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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