Methanol → HCID 86729634, compound

HRID 2284906Notes

Reaction equation

HRID 2284906 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[C:5]([Cl:18])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][C:21]=1[O:35][CH3:36].CO>C(Cl)(Cl)Cl>[Cl:18][C:5]1[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[N:7][C:2]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]3)=[CH:22][C:21]=2[O:35][CH3:36])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 552327371-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanoneHCID 59362999HCID 59362999, compound

Product 1

HCID 86729634HCID 86729634, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2,5-dichloro-4-(2-nitrophenoxy)pyrimidine (300 mg, 1.052 mmol) in 0.08M p-PTSA/1,4-dioxane (10 mL) was added 1-(4-(4-amino-3-methoxy phenyl)piperazin-1-yl)ethanone (262 mg, 1.052 mmol), and the mixture was heated to 100° C. for 16 h. TLC showed completion of starting material (TLC system: 5% methanol in chloroform (Rf): 0.4). 1,4-dioxane was evaporated under reduced pressure, and the remainder was diluted with ethyl acetate (35 mL) and the remainder was washed with water (10 mL) followed by saturated NaHCO3 solution (10 mL). The organic layer was separated, dried over sodium sulphate, and concentrated. Crude compound was purified by column chromatography using silica gel (100-200 mesh) with 3% methanol in chloroform to obtain 1-(4-(4-(5-chloro-4-(2-nitrophenoxy)pyrimidin-2-ylamino)-3-methoxyphenyl) piperazin-1-yl)ethanone as a grey solid. (Yield: 140 mg, 26.6%). MS: m/z 308.4 (ES+, M+H).

Workup

  1. custom1,4-dioxane was evaporated under reduced pressure
  2. additionthe remainder was diluted with ethyl acetate (35 mL)
  3. washthe remainder was washed with water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customCrude compound was purified by column chromatography

Sources & evidence

ORD record
ord-66f949743e3445238808b142d0d12721
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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