1-Methylpiperazine → HCID 60152865, compound

HRID 1406018Notes

Reaction equation

HRID 1406018 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]3[C:15]4[N:22]([CH3:23])[N:21]=[C:20]([C:24]([NH:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH2:33][CH3:34])=[O:25])[C:16]=4[CH2:17][CH2:18][CH2:19][C:12]3=[CH:11][N:10]=2)=[C:4]([O:35][CH3:36])[CH:3]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH3:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH2:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:24]([C:20]1[C:16]2[CH2:17][CH2:18][CH2:19][C:12]3[C:13](=[N:14][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([N:51]5[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]5)=[CH:3][C:4]=4[O:35][CH3:36])=[N:10][CH:11]=3)[C:15]=2[N:22]([CH3:23])[N:21]=1)=[O:25])[CH3:34]

Participants

7

Reactant 3

HCID 531671-MethylpiperazineHCID 68358132HCID 68358132, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 60152865HCID 60152865, compoundYield 100.8%

Reagents, catalysts & solvents 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Pd2(dba)3, (0.002 g, 0.002 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (0.002 g, 0.005 mmol), 9-[(4-bromo-2-methoxyphenyl)amino]-N-(2-ethylphenyl)-1-methyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxamide (0.040 g, 0.07 mmol) in THF (1 mL) were charged in a round-bottomed flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1M in THF, 0.9 mL) and N-methylpiperazine (0.030 mL, 0.30 mmol) were added and the reaction mixture was heated at 85° C. for 0.5 h. The reaction mixture was then allowed to cool to room temperature and concentrated. The crude solid was purified by flash chromatography on silica gel (eluant: DCM/MeOH 95/5) to afford 0.040 g (95% yield) of the title compound as yellow solid.

Workup

  1. customflushed with argon
  2. customThe flask was evacuated
  3. temperatureto cool to room temperature
  4. concentrationconcentrated
  5. customThe crude solid was purified by flash chromatography on silica gel (eluant: DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-9d3cc0d6e9a54891802fa7accd9f59bd
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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