HCID 70571586, compound → HCID 86667971, compound

HRID 2403592Notes

Reaction equation

HRID 2403592 reaction equation
[Cl:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][C:19]([C:22]4[CH:23]=[C:24]([CH:39]=[CH:40][CH:41]=4)[CH2:25][N:26]([CH3:38])[C:27](=[O:37])[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[N:17]=[CH:18][C:19]([C:22]4[CH:23]=[C:24]([CH:39]=[CH:40][CH:41]=4)[CH2:25][N:26]([CH3:38])[C:27](=[O:37])[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[CH:20][N:21]=3)[CH2:14][CH2:15]2)=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 70571586HCID 70571586, compound

Product 1

HCID 86667971HCID 86667971, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2-{[3-(2-{4-[3-chloro-5-(hydroxymethyl)pyridin-2-yl]piperazin-1-yl}pyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate (288 mg) was dissolved in dichloromethane (8 ml), and manganese dioxide (1.16 g) was added thereto, followed by stirring at room temperature for 1.5 hours. Manganese dioxide (220 mg) was added thereto, followed by additionally stirring at room temperature for 1 hour. The reaction mixture was filtered using Celite as a filtration assistant, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH=100/0 to 96/4) to obtain tert-butyl {2-[(3-{2-[4-(3-chloro-5-formylpyridin-2-yl)piperazin-1-yl]pyrimidin-5-yl}benzyl)(methyl)amino]-2-oxoethyl}carbamate (235 mg).

Workup

  1. stirringby additionally stirring at room temperature for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH=100/0 to 96/4)

Sources & evidence

ORD record
ord-7104f4b947fe419b972931eccb7fb27c
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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