1-Hydroxybenzotriazole → N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-N-methyl-acetamide
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[Cl:33][C:34]1[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[CH:41][C:35]=1[O:36][CH2:37][C:38]([OH:40])=O.[Cl:49][C:50]1[CH:51]=[C:52]([NH:64][CH3:65])[CH:53]=[CH:54][C:55]=1[O:56][CH2:57][CH2:58][N:59]([CH2:62][CH3:63])[CH2:60][CH3:61].C(N(C(C)C)C(C)C)C>C1COCC1>[Cl:49][C:50]1[CH:51]=[C:52]([N:64]([CH3:65])[C:38](=[O:40])[CH2:37][O:36][C:35]2[CH:41]=[CH:42][C:43]([C:45]([F:48])([F:47])[F:46])=[CH:44][C:34]=2[Cl:33])[CH:53]=[CH:54][C:55]=1[O:56][CH2:57][CH2:58][N:59]([CH2:62][CH3:63])[CH2:60][CH3:61]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
293 mg (0.911 mmol) of TBTU and 123 mg (0.911 mmol) of HOBT were added to a suspension of 231 mg (0.911 mmol) of (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (intermediate product Z2b) in 5 mL abs. THF and the mixture was stirred for 10 minutes at RT. 180 mg (0.701 mmol) of [3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-methyl-amine and 0.18 mL (1.051 mmol) of ethyl-diisopropylamine were added, the mixture was stirred for 16 hours at RT and evaporated down i. vac. The residue was purified by column chromatography (silica gel, silica gel, dichloromethane/MeOH/conc. aqueous ammonia 85:15:1).
Workup
- customevaporated down i
- customThe residue was purified by column chromatography (silica gel, silica gel, dichloromethane/MeOH/conc. aqueous ammonia 85:15:1)
Sources & evidence
- ORD record
- ord-ba63c41e50914e5d813cceb8f7100a3b
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351719B2
Reaction notes
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