Cyclopropanemethanamine → HCID 9901636, compound

HRID 1355354Notes

Reaction equation

HRID 1355354 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.[NH2:22][CH2:23][CH:24]1[CH2:26][CH2:25]1>O1CCOCC1>[CH:24]1([CH2:23][NH:22][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)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 18506776HCID 18506776, compound

Product 1

HCID 9901636HCID 9901636, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 150 mg (0.50 mmol) of 3-methylsulfanyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile as prepared in example 1b and 74 mg (1.0 mmol) of aminomethyl-cyclopropane in 5 ml of dioxane was stirred at 120° C. overnight. The solution was evaporated under reduced pressure and the residue was chromatographed on silica gel with a 98:2 v/v mixture of dichloromethane and methanol as the eluent. There were obtained 57 mg (35% of theory) of 3-(cyclopropylmethyl-amino)-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile as a white solid; MS: 321 (M+H)+.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel with a 98:2 v/v mixture of dichloromethane and methanol as the eluent

Sources & evidence

ORD record
ord-4f0136e8b22f46a785dcc6610a9df068
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

Loading…