Diisopropylethylamine → HCID 86760638, compound

HRID 898567Notes

Reaction equation

HRID 898567 reaction equation
C(N(C(C)C)C(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([NH2:25])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[Cl:26][C:27]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:28]=1[O:29][CH:30]([CH3:34])[C:31](O)=[O:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[ClH:10].[Cl:10][C:11]1[CH:12]=[C:13]([NH:25][C:31](=[O:32])[CH:30]([O:29][C:28]2[CH:35]=[CH:36][C:37]([C:39]([F:41])([F:40])[F:42])=[CH:38][C:27]=2[Cl:26])[CH3:34])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 68876751HCID 68876751, compound

Product 1

HCID 86760638HCID 86760638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.342 mL (2.000 mmol) of ethyl-diisopropylamine was added to a solution of 0.364 g (1.500 mmol) of 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine (intermediate product Z1b), 0.403 g (1.500 mmol) of 2-(2-chloro-4-trifluoromethyl-phenoxy)-propionic acid and 0.562 g (1.750 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 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-ab4f484b34eb432e9cd9fb0c2ca11d3d
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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