Diisopropylethylamine → HCID 178513377, compound

HRID 1994141Notes

Reaction equation

HRID 1994141 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]#[N:26])[CH:20]=3)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].Cl.[NH2:33][OH:34].CCN(C(C)C)C(C)C>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:33][OH:34])=[NH:26])[CH:20]=3)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:29])[F:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58674292HCID 58674292, compound

Product 1

HCID 178513377HCID 178513377, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanamide (0.300 g, 0.67 mmol), hydroxylamine hydrochloride (0.117 g, 1.69 mmol), and DIPEA (0.117 mL, 0.67 mmol) in MeOH was allowed to stir at rt overnight. The mixture was concentrated and purified by column chromatography to give A-85 (68 mg). 1H NMR (300 MHz, d6 DMSO) δ: 10.48 (br s, 1H), 10.17 (br s, 1H), 8.50 (d, 1H), 8.14-8.20 (m, 1H), 7.77-7.85 (m, 1H), 7.60-7.66 (m, 1H), 7.50-7.56 (m, 1H), 7.39-7.47 (m, 1H), 7.20-7.26 (m, 1H), 7.01-7.13 (m, 3H), 2.92-3.01 (m, 2H), and 2.65-2.72 (m, 2H). LCMS, FA: Rt=1.98 min, [MH+ 479.3].

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography
  3. customto give A-85 (68 mg)

Sources & evidence

ORD record
ord-3629154f226e41409dbff0ac77283545
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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