Methylamine → HCID 18698000, compound

HRID 2289559Notes

Reaction equation

HRID 2289559 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29](Cl)[N:28]=[CH:27][N:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:32][NH2:33]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29]([NH:33][CH3:32])[N:28]=[CH:27][N:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 18698045HCID 18698045, compound

Product 1

HCID 18698000HCID 18698000, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-bromophenylsulphonyl)-4-[1-(6-chloropyrimidin-4-yl)-piperazin-4-ylcarbonyl]piperazine (1.20 g) in 33% methylamine in ethanol (35 ml) was heated at 110° C. in a Carius tube for 16 hours. The mixture was evaporated to dryness and then dissolved in dichloromethane and washed with saturated aqueous ammonium chloride solution, dried (Na2SO4) and evaporated. The residue was recrystallised from methanol/ethyl acetate to give, as a solid 1-(4-bromophenylsulphonyl)4-[1-(6-methylaminopyrimidin-4-yl)-piperazin-4-ylcarbonyl]piperazine (0.65 g), mp 219-221° C. Found C, 45.80; H, 5.10 and N, 18.50%. C20H26BrN7O3S requires C, 45.80; H, 5.00 and N, 18.70% NMR (CDCl3): 2.85 (d, 3H), 3.00 (m, 4H), 3.30 (m, 4H), 3.40 (m, 4H), 3.60 (m, 4H). 4.75 (m, 1H), 5.40 (s, 1H), 7.60 (d, 2H), 7.70 (d, 2H) and 8.15 (s, 1H); m/z 524 (M+1).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in dichloromethane
  3. washwashed with saturated aqueous ammonium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-03f278e216d34de5a89beabd551693dc
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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