Methylamine → HCID 178485847, compound

HRID 1408424Notes

Reaction equation

HRID 1408424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH2:14].C([C:22]1[NH:23][CH:24]=CN=1)(C1NC=CN=1)=O.CN.C1C[O:32]CC1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:24]([NH:23][CH3:22])=[O:32]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178509482HCID 178509482, compound

Product 1

HCID 178485847HCID 178485847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-5-(1H-pyrazol-3-yl)benzenemethanamine (i.e. the product of Step C of Synthesis Example 4) (2.4 g, 11.6 mmol) in THF (12 mL) and dichloromethane (12 mL) at 10° C. was added carbonyl diimidazole (2.8 g, 17.3 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then cooled to 0° C. A solution of methylamine in THF (2 M, 12.0 mL, 24 mmol) was added, and the reaction mixture was stirred at ambient temperature for 15 h. The reaction mixture was then diluted with dichloromethane, washed with water and brine, concentrated and purified by preparative TLC (2% methanol in chloroform as eluant) to provide the title product as a solid (1.0 g).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred at ambient temperature for 15 h
  3. washwashed with water and brine
  4. concentrationconcentrated
  5. custompurified by preparative TLC (2% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-1e2a5676f5774b93b10c40b6f9f39898
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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