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

HRID 598302Notes

Reaction equation

HRID 598302 reaction equation
[NH2:1]C1C=NC2C(C=1NCC(C)(O)C)=CC=C(OCC1C=CC=CC=1)C=2.C(OCC)(OCC)OCC.C(OC)(OC)(OC)CCC.[CH2:46]([O:53][C:54]1[CH:55]=[CH:56][C:57]2[C:58]3[N:66]([CH2:67][C:68]([CH3:71])([OH:70])[CH3:69])[CH:65]=[N:64][C:59]=3[CH:60]=[N:61][C:62]=2[CH:63]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>>[NH2:1][C:60]1[C:59]2[N:64]=[CH:65][N:66]([CH2:67][C:68]([CH3:71])([OH:70])[CH3:69])[C:58]=2[C:57]2[CH:56]=[CH:55][C:54]([O:53][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:63][C:62]=2[N:61]=1

Participants

5

Reactant 4

HCID 31214Ethyl orthoformateHCID 1235121,1,1-TrimethoxybutaneHCID 67050960HCID 67050960, compoundHCID 67050984(7-benzyloxy-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 57545325(4-amino-7-benzyloxy-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 method of Part G of Example 1 with triethyl orthoformate used in lieu of trimethyl orthobutyrate. The product, (7-benzyloxy-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, was treated according to the general methods of Parts H and I of Example 1 to provide (4-amino-7-benzyloxy-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white powder, mp 254-257° C.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-90042437375e4207a08544e9491b590d
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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