Acetoxyacetyl chloride → (4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 598303Notes

Reaction equation

HRID 598303 reaction equation
[NH2:1]C1C=NC2C(C=1NCC(C)(O)C)=CC=C(OCC1C=CC=CC=1)C=2.C(OCC(Cl)=O)C.C(OCC(Cl)=O)(=O)C.[CH2:41]([O:48][C:49]1[CH:50]=[CH:51][C:52]2[C:53]3[N:61]([CH2:62][C:63]([CH3:66])([OH:65])[CH3:64])[C:60]([CH2:67][O:68][CH2:69][CH3:70])=[N:59][C:54]=3[CH:55]=[N:56][C:57]=2[CH:58]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[NH2:1][C:55]1[C:54]2[N:59]=[C:60]([CH2:67][O:68][CH2:69][CH3:70])[N:61]([CH2:62][C:63]([CH3:64])([OH:65])[CH3:66])[C:53]=2[C:52]2[CH:51]=[CH:50][C:49]([O:48][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:58][C:57]=2[N:56]=1

Participants

5

Reactant 4

HCID 26297Acetoxyacetyl chlorideHCID 84189Ethoxyacetyl chlorideHCID 67050960HCID 67050960, compoundHCID 67051136(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 57545343(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Procedure

1-{[3-Amino-7-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol, prepared as described in Parts A and B of Example 54, was treated according to the general methods described in Parts C and D of Example 54 with ethoxyacetyl chloride used in lieu of acetoxyacetyl chloride in Part C. The product, (7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, was treated according to the general methods of Parts F and G of Example 54 to provide (4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white powder, mp 215.1-215.5° C.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-761199cac1d24ea6928e4e2fff038992
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

Loading…