N-methyl-2-pyrrolidone → HCID 68623570, compound

HRID 2054138Notes

Reaction equation

HRID 2054138 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](Cl)[CH:8]=2)[N:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=2)[N:3]=1.[CH3:25][C@H:26]1[CH2:31][NH:30][CH2:29][C@@H:28]([CH3:32])[NH:27]1.CN1[C:38](=[O:39])[CH2:37]CC1>>[C:38]([N:27]1[CH:28]([CH3:32])[CH2:29][N:30]([C:9]2[CH:8]=[C:7]([N:6]3[C:2]([NH2:1])=[N:3][C:4]([NH:14][C:15]4[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=4)=[N:5]3)[CH:12]=[CH:11][N:10]=2)[CH2:31][CH:26]1[CH3:25])(=[O:39])[CH3:37]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 58613334HCID 58613334, compound

Product 1

HCID 68623570HCID 68623570, compoundYield 11%

Conditions

Temperature
250 °C

Procedure

To a solution of 100 mg of N-{4-[5-Amino-1-(2-chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-phenyl}-acetamide (0.291 mMol, 1 equiv) in 5 mL of NMP was added 100 mg of cis-2,6-dimethylpiperazine (0.877 mMol, 3.0 equiv). The stirred solution was heated to 250° C. via microwave irradiation for 15 min. The reaction mixture was concentrated under vacuum by pouring and then redissolved in 5 mL of CH2Cl2 and 5 mL of DMF. To the stirred solution was added sequentially 1 mL of Hunig's base and 100 μL of acetic anhydridide. After 3 hr at 25° C., the reaction mixture was concentrated to a dark oil and purified by flash chromatography (EtOAc), yielding 15 mg of N-(4-{1-[2-(4-Acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-5-amino-1H-[1,2,4]triazol-3-ylamino}-phenyl)-acetamide (0.0323 mMol, 11% yield) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionby pouring
  3. dissolutionredissolved in 5 mL of CH2Cl2
  4. additionTo the stirred solution was added sequentially 1 mL of Hunig's base and 100 μL of acetic anhydridide
  5. concentrationthe reaction mixture was concentrated to a dark oil
  6. custompurified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-19452ddd5c0e43958d5357d5e2066af3
Source dataset
uspto-grants-2008_02
Patent number
US07329652B2

Reaction notes

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