1-Methylpiperazine → HCID 59612477, compound

HRID 1890100Notes

Reaction equation

HRID 1890100 reaction equation
ClC1N=C(N)C=NC=1.CN1CCNCC1.Cl[C:17]1[N:35]=[C:20]2[C:21]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)=[CH:22][CH:23]=[CH:24][N:19]2[N:18]=1.[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[N:47][CH:46]=[C:45]([NH2:49])[N:44]=2)[CH2:39][CH2:38]1>CN(C)C=O.O>[CH3:36][N:37]1[CH2:38][CH2:39][N:40]([C:43]2[CH:48]=[N:47][CH:46]=[C:45]([NH2:49])[N:44]=2)[CH2:41][CH2:42]1.[CH3:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([C:21]2[C:20]3[N:19]([N:18]=[C:17]([NH:49][C:45]4[N:44]=[C:43]([N:40]5[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]5)[CH:48]=[N:47][CH:46]=4)[N:35]=3)[CH:24]=[CH:23][CH:22]=2)=[CH:26][CH:27]=1)(=[O:33])=[O:32]

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 1184582-Amino-6-ChloropyrazineHCID 66520377HCID 66520377, compoundHCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 2

HCID 59612477HCID 59612477, compoundHCID 66520377HCID 66520377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-ylamine was prepared from 6-chloro-pyrazin-2-ylamine (1.00 g, 7.72 mmol) and 1-methylpiperazine (942 L, 8.49 mmol) combined in N,N-dimethylformamide (35 mL) and heated at 100° C. overnight. The reaction was poured into water and extracted with 3 portions of dichloromethane. The combined organic was dried over magnesium sulfate, filtered and evaporated to yield an off-white solid. This solid was purified via chromatography (silica gel 40 g methanol in dichloromethane). Product isolated as a tan oil that solidified upon standing. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 7.33 (s, 1H), 7.16 (s, 1H), 5.93 (s, 2H), 3.40 (s, 4H), 2.36 (s, 4H), 2.20 (s, 3H). 386b) [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-yl)-amine was prepared from 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (133 mg, 0.434 mmol) and 4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-ylamine (92.159 mg, 0.47689 mmol) in a manner analogous to Example 2d. Product isolated as an off-white foam (28.64 mg, 14.2%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.07 (s, 1H), 8.91 (d, J=6.6 Hz, 1H), 8.59 (s, 1H), 8.41 (d, J=8.5 Hz, 2H), 8.08 (d, J=8.3 Hz, 2H), 8.00 (d, J=7.6 Hz, 1H), 7.83 (s, 1H), 7.23 (t, J=14.5, 7.4 Hz, 1H), 3.32 (s, 3H), 3.56 (s, 4H), 2.40 (s, 4H), 2.23 (s, 3H). MS=465 (MH)+.

Workup

  1. extractionextracted with 3 portions of dichloromethane
  2. dry with materialThe combined organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield an off-white solid
  6. customThis solid was purified via chromatography (silica gel 40 g methanol in dichloromethane)
  7. customProduct isolated as a tan oil that

Sources & evidence

ORD record
ord-6df772ed35584a0eb43f61ae62b4aed3
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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