1-Methylpiperazine → HCID 68463146, compound

HRID 501207Notes

Reaction equation

HRID 501207 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[S: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: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[S: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:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86607546HCID 86607546, compound

Product 1

HCID 68463146HCID 68463146, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of methyl-2-{8-[5-(formyl)-thien-2-yl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.09 g, 0.21 mmol) in DCM (50 mL) was added Na(OAc)3BH (0.114 g, 0.53 mmol) and stirred for 10 min. To the reaction mixture was added N-methylpiperazine (0.107 g, 1.07 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 (100 mL) and water (15 mL) and the organic layer was separated, washed with water (2×10 mL), dried over sodium sulphate 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)-thien-2-yl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.08 g).

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 (100 mL) and water (15 mL)
  4. customthe organic layer was separated
  5. washwashed with water (2×10 mL)
  6. dry with materialdried over sodium sulphate
  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-a39b25bdca65404c9bdde14466860e29
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

Loading…