1-Methylpiperazine → HCID 11852567, compound

HRID 551856Notes

Reaction equation

HRID 551856 reaction equation
[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[C:13]([CH3:36])=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=4)[C:21](=[O:34])[N:20]([CH3:35])[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:75][N:76]1[CH2:81][CH2:80][NH:79][CH2:78][CH2:77]1>O.CN(C)C=O>[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([C:29]([N:79]5[CH2:80][CH2:81][N:76]([CH3:75])[CH2:77][CH2:78]5)=[O:30])=[CH:32][CH:33]=4)[C:21](=[O:34])[N:20]([CH3:35])[CH:19]=3)[C:13]=2[CH3:36])=[O:10])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 248572334-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid

Product 1

HCID 11852567HCID 11852567, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid (7) (80 mg; 0.16 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (69 mg; 0.16 mmol), N,N-diisopropylethylamine (0.09 mL; 0.48 mmol), and N,N-dimethylformamide (1 mL) was stirred at room temperature for 0.5 hr. N-Methylpiperazine (80 mg; 0.8 mmol) was added and the mixture was stirred at room temperature for 16 hr. Water (30 mL) was added and the mixture was extracted with ethyl acetate (3×60 mL). The combined organic extracts were washed with water (2×30 mL) and brine (1×30 mL), dried over magnesium sulfate, and evaporated under reduced pressure. The residue was slurried with diethyl ether and filtered to give 4-tert-butyl-N-(2-methyl-3-{4-methyl-6-[4-(4-methyl-piperazine-1-carbonyl)-phenylamino]-5-oxo-4,5-dihydro-pyrazin-2-yl}-phenyl)-benzamide (8) as a cream solid (50 mg), MS 593.35 (M+H)

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×60 mL)
  2. washThe combined organic extracts were washed with water (2×30 mL) and brine (1×30 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. filtrationfiltered

Sources & evidence

ORD record
ord-adbbd03b6ab9460c9ad63737e9d45f4b
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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