Trifluoroacetic acid → HCID 86622809, compound

HRID 1641908Notes

Reaction equation

COC1C=CC(C([NH:18][C:19]2[N:27]=[C:26]([Cl:28])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:29]2[CH2:33][C@H:32]([N:34]3[CH:38]=[C:37]([CH3:39])[CH:36]=[N:35]3)[C@@H:31]([OH:40])[C@H:30]2[OH:41])C2C=CC(OC)=CC=2)=CC=1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[NH2:18][C:19]1[N:27]=[C:26]([Cl:28])[N:25]=[C:24]2[C:20]=1[N:21]=[CH:22][N:23]2[C@@H:29]1[CH2:33][C@H:32]([N:34]2[CH:38]=[C:37]([CH3:39])[CH:36]=[N:35]2)[C@@H:31]([OH:40])[C@H:30]1[OH:41]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86622810HCID 86622810, compound

Product 1

HCID 86622809HCID 86622809, compound

Procedure

(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(4-methyl-pyrazol-1-yl)-cyclopentane-1,2-diol (Intermediate BB1) (0.020 g, 35 μmol) is dissolved in TFA (200 μL). The reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 2 hours. The solvent is removed in vacuo and the title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water—0.1% TFA). 1H nmr (MeOD, 400 MHz); 8.50 (s, 1H), 7.85 (s, 1H), 7.55 (s, 1H), 4.95 (m, 1H), 4.70 (m, 1H), 4.65 (m, 1H), 4.30 (m, 1H), 2.95 (m, 1H), 2.65 (m, 1H), 2.15 (s, 3H), MS (ES+) m/e 350 (MH+).

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-798df6a2b9cf4735a7a88a7ea737dcf5
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114877B2

Reaction notes

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