Sodium triacetoxyborohydride → Methyl [4-({[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl][2-(dimethylamino)ethyl]amino}methyl)phenyl]acetate

HRID 2090242Notes

Reaction equation

HRID 2090242 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][CH2:25][CH2:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:32][CH:31]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1>[CH3:40][O:39][C:37](=[O:38])[CH2:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:28][N:18]([CH2:17][CH2:16][CH2:15][N:14]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 19363032Methyl 2-(4-formylphenyl)acetate2×HCID 68432302N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

Product 1

HCID 25106606Methyl [4-({[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl][2-(dimethylamino)ethyl]amino}methyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of the product from step (vi) (0.25 g), methyl (4-formylphenyl)acetate (0.15 g) and sodium triacetoxyborohydride (0.2 g) in NMP (10 mL) was stirred at rt for 18 h then heated at 45° C. for 3 h. A further portion of methyl(4-formylphenyl)acetate (0.1 g) and sodium triacetoxyborohydride (0.2 g) were added then stirred at 45° C. for 6 h. The mixture was purified by RPHPLC, yield 0.035 g.

Workup

  1. temperaturethen heated at 45° C. for 3 h
  2. stirringthen stirred at 45° C. for 6 h
  3. customThe mixture was purified by RPHPLC, yield 0.035 g

Sources & evidence

ORD record
ord-759a726ff7d542ea8d7e7beb65ca4ac0
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

Loading…