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Diisopropylethylamine → 1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4'-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide

HRID 39180
Notes
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Reaction equation

HRID 39180 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)([CH3:24])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH2:23])[CH:17]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[O:33]1[C:37]2[CH:38]=[CH:39][C:40]([C:42]3([C:45](O)=[O:46])[CH2:44][CH2:43]3)=[CH:41][C:36]=2[O:35][CH2:34]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)([CH3:24])[C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH:23][C:45]([C:42]4([C:40]5[CH:39]=[CH:38][C:37]6[O:33][CH2:34][O:35][C:36]=6[CH:41]=5)[CH2:44][CH2:43]4)=[O:46])[CH:17]=3)=[CH:14][CH:15]=2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 671206764'-[Bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamine

Product 1

HCID 671206751-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4'-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Conditions

Temperature
65 °C

Procedure

4′-[Bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamine (˜10 mmol) and 1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (2.28 g, 11 mmol) were dissolved in chloroform (25 mL) followed by addition of TCPH (4.1 g, 12 mmol) and DIEA (5.0 mL, 30 mmol). The reaction mixture was heated at 65° C. for 48 h. The volatiles were removed under reduced pressure. The residue was distributed between water (200 mL) and ethyl acetate (150 mL). The organic layer was washed with 5% NaHCO3 (2×150 mL), water (1×150 mL), brine (1×150 mL) and dried over MgSO4. Evaporation of the solvent yielded crude 1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4′-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide as a pale oil, which was used without further purification. ESI-MS m/z calc. 629.0, found 630.0 (M+1) (HPLC purity ˜85-90%, UV254 nm).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. washThe organic layer was washed with 5% NaHCO3 (2×150 mL), water (1×150 mL), brine (1×150 mL)
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-00d92a98754e46dd90deba1e842a19d2
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524767B2

Reaction notes

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