Potassium → 2-[2-(2-{2-[2-(2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy]-ethoxy)-ethoxy}-ethoxy]-ethoxy)-ethanol

HRID 1255971

Reaction equation

HRID 1255971 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:30])[CH:3]=1.ClC1C(Cl)=CC(NC2C3C(=CC(F)=C([N+]([O-])=O)C=3)N=CN=2)=C(F)C=1.C([Si](C)(C)[O:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71]OCCOCCO)(C)(C)C.[K]>CS(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:71][CH2:70][O:69][CH2:68][CH2:67][O:66][CH2:65][CH2:64][O:63][CH2:62][CH2:61][OH:60])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:30])[CH:3]=1

Participants

6

Reactant 4

HCID 5462222PotassiumHCID 111761854-[(3,4-Dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazolineHCID 118254402,2,3,3-Tetramethyl-4,7,10,13,16,19-hexaoxa-3-silahenicosan-21-ol2×HCID 692669552-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol

Product 1

HCID 692615262-[2-(2-{2-[2-(2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy]-ethoxy)-ethoxy}-ethoxy]-ethoxy)-ethanolYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 29c was prepared as described hereinabove for Compound 29a, using Compound 25 (0.596 gram, 1.6 mmol), 2-[2-(2-{2-[2-(2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy}-ethoxy]-ethanol (Compound 28c, 0.957 gram, 2.4 mmol), and potassium trimethylsilonate (0.621 gram, 4.74 mmol) dissolved in DMSO (37 ml). The crude residue was purified by silica gel column chromatography, using a mixture of 2% methanol in dichloromethane as eluent, to obtain Compound 29c (0.568 gram, 56%).

Workup

  1. customCompound 29c was prepared
  2. customThe crude residue was purified by silica gel column chromatography
  3. additiona mixture of 2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-aa13f2da1f004efd90839764b8bbc928
Source dataset
uspto-grants-2013_06
Patent number
US08461166B2

Linked notes

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