Ethoxyacetyl chloride → N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

HRID 2383116Notes

Reaction equation

HRID 2383116 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])([CH3:16])[CH3:15])=[CH:9][CH:8]=[C:7]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:6]=2.C(OC(=O)NCCCCNC1C2C(=[CH:47][C:48]([O:52][CH2:53][C:54]3C=CC=CC=3)=CC=2)N=CC=1N)(C)(C)C.C(OCC(Cl)=O)C.COCCC(Cl)=O>ClCCl>[CH2:23]([O:22][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])([CH3:16])[CH3:15])[C:47]([CH2:48][O:52][CH2:53][CH3:54])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 84189Ethoxyacetyl chlorideHCID 27597283-Methoxypropanoyl chlorideHCID 67050976N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamideHCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate

Product 1

HCID 67051174N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A modification of the general method described in Part C of Example 50 was followed using N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamide (12.6 g, 30.4 mmol) in lieu of tert-butyl{-4-[3-amino-7-(benzyloxy)quinolin-4-ylamino]butyl}carbamate and ethoxyacetyl chloride (3.33 mL, 30.4 mmol) in lieu of methoxypropionyl chloride. The crude product was dissolved in dichloromethane (300 mL), and the resulting solution was washed with water (2×100 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The oil was purified by column chromatography on silica gel (eluting with 97.5:2.5 chloroform:methanol) to provide 12.4 g of N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a beige foam.

Workup

  1. washthe resulting solution was washed with water (2×100 mL) and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto provide a brown oil
  6. customThe oil was purified by column chromatography on silica gel (eluting with 97.5:2.5 chloroform:methanol)

Sources & evidence

ORD record
ord-5f6eac163e2d42aebd8087342fe9c06e
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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