HCID 57970179, compound → HCID 57970081, compound

HRID 1666652Notes

Reaction equation

HRID 1666652 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[N:23]=[C:22]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[N:23]=[C:22]([N:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 57970179HCID 57970179, compound

Product 1

HCID 57970081HCID 57970081, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

t-Butyl 4-(2-((S)-1-benzylpyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (26 g) was dissolved in methanol (260 mL), followed by addition of 20% Pd(OH)2/C (5.2 g), and the mixture was stirred under hydrogen atmosphere at room temperature for 16 h and at 50° C. for 8 h. 20% Pd(OH)2/C (5.2 g) was further added, and the mixture was stirred under hydrogen atmosphere for 3 days. The catalyst was removed by filtration, then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/a solution of 1 M ammonium in methanol=9:1) to obtain the title compound (6.3 g).

Workup

  1. stirringthe mixture was stirred under hydrogen atmosphere for 3 days
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/a solution of 1 M ammonium in methanol=9:1)

Sources & evidence

ORD record
ord-01c468952a544ba6b9ba73f8e5cd9ac9
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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