Methanol → HCID 71715144, compound

HRID 928255Notes

Reaction equation

HRID 928255 reaction equation
[S:1](=[O:30])(=[O:29])([O:3][CH2:4][C@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH:19]=[C:15]3[N:14]=[C:13](Cl)[CH:12]=2)[C@H:7]([OH:27])[C@@H:6]1[OH:28])[NH2:2].CO>[Pd]>[S:1](=[O:30])(=[O:29])([O:3][CH2:4][C@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH:19]=[C:15]3[N:14]=[CH:13][CH:12]=2)[C@H:7]([OH:27])[C@@H:6]1[OH:28])[NH2:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 71715143HCID 71715143, compound

Product 1

HCID 71715144HCID 71715144, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(rac)-[(1R,2R,3S,4R)-4-{[5-chloro-2-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}-2,3-dihydroxycyclopentyl]methyl rel-sulfamate (5.0 mg, 0.011 mmol; synthesized following Steps 1-4 of Method D starting from 5-pyridin-2-yl-2H-pyrazol-3-ylamine) is dissolved in methanol (1.00 mL, 0.0247 mol). Palladium on carbon (10%, 29.2 mg, 0.00275 mmol) is added and the suspension is purged with hydrogen gas and stirred for 3 days at room temperature under a balloon of hydrogen (1 atm). The reaction mixture is purged with nitrogen, filtered through celite and rinsed with methanol. The filtrate is concentrated in vacuo and purified by preparative HPLC to provide (rac)-[(1R,2R,3S,4R)-2,3-dihydroxy-4-{[2-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}cyclopentyl]methyl rel-sulfamate (1.0 mg, yield 22%). LCMS: (AA) M+1 421; 1H NMR (400 MHz, MeOD) δ 8.72-8.61 (m, 1H), 8.25 (d, J=7.8 Hz, 1H), 8.18 (d, J=4.8 Hz, 1H), 7.99-7.88 (m, 1H), 7.47-7.37 (m, 1H), 7.01 (s, 1H), 6.41-6.32 (m, 1H), 4.30-4.18 (m, 2H), 4.16-3.92 (m, 3H), 2.61-2.49 (m, 1H), 2.48-2.35 (m, 1H), 1.68-1.56 (m, 1H).

Workup

  1. customthe suspension is purged with hydrogen gas
  2. customThe reaction mixture is purged with nitrogen
  3. filtrationfiltered through celite
  4. washrinsed with methanol
  5. concentrationThe filtrate is concentrated in vacuo
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6a8a964054a644e7a6819562aed555cc
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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