1-(Methanesulfonyl)piperidin-4-amine → HCID 67426785, compound

HRID 1516437Notes

Reaction equation

HRID 1516437 reaction equation
[I:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)(=[O:23])=[O:22]>O1CCOCC1>[I:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:30][CH:27]4[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]4)[N:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 113558261-(Methanesulfonyl)piperidin-4-amineHCID 68604454HCID 68604454, compound

Product 1

HCID 67426785HCID 67426785, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-iodo-1-(2-methanesulfinyl-pyrimidin-4-yl)-1H-benzotriazole (700 mg) and 1-methanesulfonyl-piperidin-4-ylamine (642 mg) in 1,4-dioxane (20 mL) was stirred under argon, then heated at 110° C. for 4.5 h. The reaction mixture was then cooled, and the solvent removed in vacuo to provide a solid. The solid was chromatographed on silica using 0-100% EtOAc/hexanes to provide [4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl]-(1-methanesulfonyl-piperidin-4-yl)-amine (731 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe solvent removed in vacuo
  3. customto provide a solid
  4. customThe solid was chromatographed on silica using 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-cdf7db7ae09d4209983a074811d144e1
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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