Triethylamine → methanesulfonic acid 2-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazolin-7-yloxy]-ethoxy}-ethyl ester

HRID 1255972Notes

Reaction equation

HRID 1255972 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.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[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][S:39]([CH3:38])(=[O:41])=[O:40])=[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

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 692669552-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol

Product 1

HCID 86618842methanesulfonic acid 2-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazolin-7-yloxy]-ethoxy}-ethyl esterYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 29a (0.035 gram, 0.076 mmol) was dissolved in dichloromethane (4.3 ml) and triethylamine (0.032 gram, 3.82 mmol) was added to the resulting solution. Methanesulfonyl chloride (MsCl, 0.025 gram, 0.022 mmol) was then added and the resulting mixture was stirred at room temperature for 3 hours. The mixture was thereafter extracted twice with CH2Cl2, washed with brine and dried over sodium sulfate. The crude residue was purified by silica gel column chromatography, using a mixture of 2% methanol in dichloromethane as eluent, to give Compound 32a (0.012 gram, 29% yield).

Workup

  1. extractionThe mixture was thereafter extracted twice with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe crude residue was purified by silica gel column chromatography
  5. additiona mixture of 2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-b82539dee92c4eb18b087b6a469bbbd4
Source dataset
uspto-grants-2013_06
Patent number
US08461166B2

Reaction notes

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