p-Toluenesulfonic acid → 5'-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2'-(isopropoxymethyl)-N,N-dimethylbiphenyl-4-carboxamide

HRID 1665739Notes

Reaction equation

HRID 1665739 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH2:33][OH:34])=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH3:32])[CH3:31])=[O:29])=[CH:24][CH:23]=5)[CH:21]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:35]1(C)[CH:40]=CC(S(O)(=O)=O)=C[CH:36]=1>C(O)(C)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH2:33][O:34][CH:35]([CH3:40])[CH3:36])=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH3:31])[CH3:32])=[O:29])=[CH:24][CH:23]=5)[CH:21]=4)=[O:14])[CH2:11][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 592065855'-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2'-(hydroxymethyl)-N,N-dimethylbiphenyl-4-carboxamide

Product 1

HCID 592066525'-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2'-(isopropoxymethyl)-N,N-dimethylbiphenyl-4-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5′-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2′-(hydroxymethyl)-N,N-dimethylbiphenyl-4-carboxamide (46 mg, 0.10 mmol) and para-toluenesulfonic acid (38 mg, 0.2 mmol) were dissolved in isopropanol (1.0 mL) and irradiated in the microwave at 140° C. for 10 minutes. Volatiles were removed in vacuo and crude product was purified by reverse phase HPLC to afford the pure product (22 mg, 44%). ESI-MS m/z calc. 500.2, found 501.3 (M+1)+; retention time 3.30 minutes.

Workup

  1. customirradiated in the microwave at 140° C. for 10 minutes
  2. customVolatiles were removed in vacuo and crude product
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-cc755b5c75da4e3792615b112b28b2c3
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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