1-Methylpiperazine → HCID 21945780, compound

HRID 1609895Notes

Reaction equation

HRID 1609895 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH3:22])[C:17]([C:19](O)=[O:20])=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH3:22])[C:17]([C:19]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)=[O:20])=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9839229HCID 9839229, compound

Product 1

HCID 21945780HCID 21945780, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 20 (7 mg, 0.023 mmol) in DMF (0.4 mL) at 25° C. was added N-methyl piperazine (3.5 μL, 0.03 mmol), 1-hydroxybenzotriazole (3 mg, 0.023 mmol) and 1 (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7 mg, 0.05 mmol). After 24 hrs., the mixture was concentrated, diluted with water (2 mL), and extracted with ethyl acetate (5×2 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (2×5 mL). The crude material was purified by chromatography on silica gel eluting with a gradient of 5–10% methanol in chloroform to provide 6.23 mg (70%) of the title compound as white solid. MS: [M+H]+=381.3; 1H NMR (CDCl3): δ7.76 (s, 1H), 7.48 (s, 1H), 7.08 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.69 (d, J=8.2 Hz, 1H), 3.82-3.44 (m, 2H), 2.54 (s, 3H), 2.53-2.28 (m, 6H), 2.27 (s, 3H), 2.10 (s, 3H)

Workup

  1. concentration, the mixture was concentrated
  2. additiondiluted with water (2 mL)
  3. extractionextracted with ethyl acetate (5×2 mL)
  4. washThe combined organic extracts were washed with saturated aqueous NaHCO3 (2×5 mL)
  5. customThe crude material was purified by chromatography on silica gel eluting with a gradient of 5–10% methanol in chloroform

Sources & evidence

ORD record
ord-91dbd6ce531d4708ad72266a8a0e0ecb
Source dataset
uspto-grants-2006_01
Patent number
US06982265B1

Reaction notes

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