Trifluoroacetic acid methylene chloride → HCID 11689680, compound

HRID 1820988Notes

Reaction equation

HRID 1820988 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].C(Cl)Cl.C(O)(C(F)(F)F)=O>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68888258HCID 68888258, compound

Product 1

HCID 11689680HCID 11689680, compoundYield 86.9%

Procedure

A solution of 23 mg (0.05 mmol) of tert-butyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from Step A) in 4:1 v/v CH2Cl2/TFA was stirred at rt for 30 min. The mixture was concentrated. Purification by HPLC B gave 17 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.47 (d, J=6.2, 6H), 2.66 (s, 3H), 2.74 (t, J=7.8, 2H), 3.01 (t, J=7.8, 2H), 4.76-4.82 (m, 1H), 7.11 (d, J=9.0, 1H), 7.19-7.21 (m, 2H), 8.01 (d, J=8.3, 1H), 8.33 (dd, J=2.3, 8.9, 11H), 8.42 (d, J=2.1, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customPurification by HPLC B

Sources & evidence

ORD record
ord-f819f391049e4fd3ad7c276faea0e139
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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