1-Methylpiperazine → HCID 71223981, compound

HRID 2402955Notes

Reaction equation

HRID 2402955 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[C:10]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[N:9]=1)=[O:7])=O.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[BH3-]C#N.[Na+]>O1CCOCC1>[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([CH2:1][C:3]2[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=2)[C:6]([C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[C:10]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]4)=[CH:24][CH:25]=3)[N:9]=2)=[O:7])[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 89388365HCID 89388365, compound

Product 1

HCID 71223981HCID 71223981, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of Example 215C (100 mg, 0.2 mmol) in dioxane (5 mL) was added 1-methylpiperazine (40 mg, 0.4 mmol) and NaCNBH3 (25 mg, 0.5 mmol). The reaction mixture was stirred at 70° C. for 2 days, and concentrated. The residue was purified by flash chromatography, eluted with 0-20% gradient methanol in methylene chloride to yield the title compound. MS (DCI/NH3) m/z 557 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluted with 0-20% gradient methanol in methylene chloride

Sources & evidence

ORD record
ord-742c5229fdff4e69b7b3152a487a42a8
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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