1-Methylpiperazine → HCID 68463286, compound

HRID 501204Notes

Reaction equation

HRID 501204 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:30][CH2:29][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[O:23][C:24]([CH:27]=O)=[CH:25][CH:26]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:30][CH2:29][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[O:23][C:24]([CH2:27][N:49]6[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]6)=[CH:25][CH:26]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 87461389HCID 87461389, compound

Product 1

HCID 68463286HCID 68463286, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of methyl-2-{8-[5-(formyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.12 g, 0.29 mmol) in DCM (20 mL) was added Na(OAc)3BH (0.126 g, 0.59 mmol) and stirred for 10 min. To the reaction mixture was added N-methylpiperzine (0.149 g, 1.49 mmol) under nitrogen atmosphere and the reaction mixture was continued stirring at room temperature for 4 hr. The progress of the reaction was monitored by TLC and upon completion of the reaction the mixture was partitioned between DCM (50 mL) and water (25 mL) and the organic layer was separated, washed with water (2×25 mL), dried over sodium sulfate filtered and the solvent was removed under reduced pressure to give crude residue, which was purified by column chromatography using silica gel to provide methyl-2-{8-[5-((4-methylpiperazin-1-yl)methyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.1 g, 69.4%).

Workup

  1. stirringthe reaction mixture was continued stirring at room temperature for 4 hr
  2. customThe progress of the reaction was monitored by TLC and upon completion of the reaction the mixture
  3. customwas partitioned between DCM (50 mL) and water (25 mL)
  4. customthe organic layer was separated
  5. washwashed with water (2×25 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customto give crude residue, which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b2e5d342a9d940c4a3f2f89efea1728d
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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