Hydroxyamine hydrochloride → HCID 24760659, compound

HRID 1989666Notes

Reaction equation

HRID 1989666 reaction equation
CC1[N:3]([C:8]2[CH:13]=[C:12]([C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[C:24]([C:26]5[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=5)[CH:23]=[C:22]([CH3:36])[N:21]=4)[CH:17]=[CH:16][N:15]=3)[CH:11]=[CH:10][N:9]=2)C(C)=CC=1.Cl.NO>>[CH3:36][C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][N:15]=[C:14]([C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH2:3])[CH:13]=3)[N:19]=2)[CH:25]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)[CH:23]=1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57469049HCID 57469049, compound

Product 1

HCID 24760659HCID 24760659, compoundYield 27%

Procedure

A mixture of the above described 2-[2-(2,5-dimethyl-pyrrol-1-yl)-pyridin-4-yl]-4-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidine (280 mg, 0.577 mmol), hydroxylamine hydrochloride (200 mg, 2.89 mmol) 1.5 M NaOH-sol. (0.96 mL, 1.44 mmol) in 1-propanole (3 mL) was stirred at 120° C. for 3 h in a sealed tube. Cooled to rt, poured the reaction mixture directly on a silica gel column and chromatographed with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.050 g, 27%) as an off-white solid. MS (ISP) 408.4 [(M+H)+]; mp 217° C.

Workup

  1. additionA mixture of the
  2. additionpoured the reaction mixture directly on a silica gel column
  3. customchromatographed with EtOAc

Sources & evidence

ORD record
ord-7982240bf0c64a56b40ad3651775cead
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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