Cornforth reagent → HCID 69307294, compound

HRID 2056737Notes

Reaction equation

HRID 2056737 reaction equation
[OH:1][CH:2]1[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[C:7]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C@H:22]4[C:27]5[CH:28]=[CH:29][C:30]([C:32]([NH2:34])=[O:33])=[CH:31][C:26]=5[CH2:25][CH2:24][O:23]4)[C@H:16]([CH3:35])[CH2:15]2)=[CH:6][CH:5]=[C:4]3[CH2:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C>[CH3:35][C@@H:16]1[CH2:15][N:14]([C:7]2[C:8]3[C:13]4[C:4]([CH2:3][C:2](=[O:1])[C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:5][CH:6]=2)[CH2:19][CH2:18][N:17]1[CH2:20][CH2:21][C@H:22]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([NH2:34])=[O:33])=[CH:31][C:26]=2[CH2:25][CH2:24][O:23]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagent2×HCID 69306565HCID 69306565, compound

Product 1

HCID 69307294HCID 69307294, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S)-1-{2-[(2R)-4-(1-hydroxy-1,2-dihydro-5-acenaphthylenyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carboxamide (0.10 g, 0.21 mmol) in dry DMF (2 mL), cooled to 0° C. under nitrogen, was added pyridinium dichromate (0.08 g, 0.21 mmol), and the mixture stirred for 4 h, allowing the reaction to warm to room temperature. A further equivalent of pyridinium dichromate was added and the reaction stirred for a further 1 h. The mixture was poured onto water and the resultant precipitate filtered off. Purification by preparative LC-MS yielded (1S)-1-{2-[(2R)-2-methyl-4-(1-oxo-1,2-dihydro-5-acenaphthylenyl)piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carboxamide. M+H=470.

Workup

  1. customthe reaction
  2. stirringthe reaction stirred for a further 1 h
  3. additionThe mixture was poured onto water
  4. filtrationthe resultant precipitate filtered off
  5. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-e0f14568b1ed4aa19d48534bad51a87b
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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