Triethylamine → (e)-n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

HRID 898563Notes

Reaction equation

HRID 898563 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]([NH2:24])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21].[Cl:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1/[CH:36]=[CH:37]/[C:38](O)=[O:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:38](=[O:39])/[CH:37]=[CH:36]/[C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:34])([F:33])[F:35])=[CH:31][C:26]=2[Cl:25])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 5709520HCID 5709520, compoundHCID 688758613-Chloro-4-[2-(diethylamino)ethoxy]aniline hydrochloride

Product 1

HCID 59691664(e)-n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.29 mL (2.10 mmol) of triethylamine was added to a solution of 0.28 g (1.00 mmol) of 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine-hydrochloride (intermediate product Z1b), 0.25 g (1.00 mmol) of (E)-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylic acid (Z37b) and 0.34 g (1.05 mmol) of TBTU in 10 mL abs. THF and the mixture was stirred for 1 hour at RT. The reaction mixture was evaporated down i. vac. and the residue was combined with dichloromethane and water. The org. phase was separated off, washed with sat. aqueous sodium bicarbonate solution and water and evaporated down i. vac. The residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95).

Workup

  1. customThe reaction mixture was evaporated down i
  2. customphase was separated off
  3. washwashed with sat. aqueous sodium bicarbonate solution and water
  4. customevaporated down i
  5. customThe residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95)

Sources & evidence

ORD record
ord-98a1bdf123114b2884dca418e10e2487
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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