Trifluoroacetic acid → 1-[6-Amino-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide

HRID 2382457Notes

Reaction equation

HRID 2382457 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[C@@H:19]3[CH2:23][C@H:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])[C@@H:21]([OH:29])[C@H:20]3[OH:30])=[C:12]([NH:31]C(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)[N:11]=2)[CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[C@@H:19]3[CH2:23][C@H:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])[C@@H:21]([OH:29])[C@H:20]3[OH:30])=[C:12]([NH2:31])[N:11]=2)[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666306851-[6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide

Product 1

HCID 666309031-[6-Amino-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 1-[6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide (0.08 g, 0.122 mmol) in dry dichloromethane (4 ml) is treated slowly with trifluoroacetic acid (2 ml). The reaction mixture is stirred at room temperature for 48 h and then concentrated in vacuo. The residue was co-evaporated with chloroform three times to remove excess trifluoro acetic acid and purification of the crude product by preparative HPLC affords the title compound. LC-MS (0.1% formic acid, acetonitrile): (MH+ 430.28)

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove excess
  3. customtrifluoro acetic acid and purification of the crude product by preparative HPLC

Sources & evidence

ORD record
ord-a449ac79321e4782bcf7de97529e272f
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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