m-Chloroperbenzoic acid → HCID 9947613, compound

HRID 1355359Notes

Reaction equation

HRID 1355359 reaction equation
CS[C:3]1[N:4]=[N:5][C:6]([C:20]#[N:21])=[C:7]([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH2:11][CH2:10]2)[N:8]=1.ClC1C=CC=C(C(OO)=O)C=1.CS(C1N=NC(C#N)=C(N2CCC3C=CC=CC=3CC2)N=1)(=O)=O.[NH2:56][CH2:57][CH2:58][C:59]1[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=1>ClCCl.O1CCOCC1>[N:61]1[CH:62]=[CH:63][CH:64]=[C:59]([CH2:58][CH2:57][NH:56][C:3]2[N:4]=[N:5][C:6]([C:20]#[N:21])=[C:7]([N:9]3[CH2:15][CH2:14][C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][CH2:10]3)[N:8]=2)[CH:60]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 11221182HCID 11221182, compoundHCID 18506776HCID 18506776, compound

Product 1

HCID 9947613HCID 9947613, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 120 mg (0.40 mmol) of 3-methylsulfanyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile in 5 ml of dichloromethane was treated at room temperature with 109 mg (0.44 mmol) of 3-chloro-perbenzoic acid (70%). After 2 hours the reaction mixture was evaporated under reduced pressure, and, without working-up and characterization, the resulting crude 3-methanesulfonyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile was directly treated with a solution of 108 mg (0.88 mmol) of 3-(2-aminoethyl)pyridine in 10 ml of dioxane. The reaction mixture was then stirred at 80° C. overnight. The reaction mixture was then evaporated under reduced pressure and the residue obtained directly chromatographed on silica gel with a 95:5:0.1 v/v/v mixture of dichloromethane, methanol and ammonium hydroxide as the eluent. There were obtained 55 mg (37% of theory) of 3-(2-pyridin-3-yl-ethylamino)-5 -(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile as a white amorphous solid; MS: 372 (M+H)+.

Workup

  1. customAfter 2 hours the reaction mixture was evaporated under reduced pressure
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customthe residue obtained directly
  4. customchromatographed on silica gel with a 95:5:0.1 v/v/v mixture of dichloromethane, methanol and ammonium hydroxide as the eluent

Sources & evidence

ORD record
ord-2c309a29f7f041a29b3b559ce0552ea5
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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