Trifluoroacetic acid → isoquinoline-1-carboxylic acid {1-[(2-hydroxy-5-oxo-tetra-hydrofuran-3-ylcarbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl} amide

HRID 891192Notes

Reaction equation

HRID 891192 reaction equation
C([O:3][CH:4]1[CH:8]([NH:9][C:10]([CH2:12][N:13]2[CH2:19][CH:18]=[CH:17][CH2:16][CH:15]([NH:20][C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][N:24]=3)=[O:22])[C:14]2=[O:33])=[O:11])[CH2:7][C:6](=[O:34])[O:5]1)C.FC(F)(F)C(O)=O>CC#N.O>[OH:3][CH:4]1[CH:8]([NH:9][C:10]([CH2:12][N:13]2[CH2:19][CH:18]=[CH:17][CH2:16][CH:15]([NH:20][C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][N:24]=3)=[O:22])[C:14]2=[O:33])=[O:11])[CH2:7][C:6](=[O:34])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590750isoquinoline-1-carboxylic acid {1-[(2-ethoxy-5-oxo-tetra-hydrofuran-3-ylcarbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl} amide

Product 1

HCID 75025996isoquinoline-1-carboxylic acid {1-[(2-hydroxy-5-oxo-tetra-hydrofuran-3-ylcarbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl} amide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of isoquinoline-1-carboxylic acid {1-[(2-ethoxy-5-oxo-tetra-hydrofuran-3-ylcarbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl} amide, 6, from above in CH3CN/H2O is added trifluoroacetic acid. After stirring for 30 minutes the solution is concentrated in vacuo and the crude product purified by preparative reverse phase HPLC to afford the desired product.

Workup

  1. concentrationis concentrated in vacuo
  2. customthe crude product purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-460d2057d4e04209a19a070ff7e863c1
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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