HCID 89758788, compound → HCID 71715656, compound

HRID 928252Notes

Reaction equation

HRID 928252 reaction equation
[S:1](=[O:31])(=[O:30])([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][CH:21]=4)[CH:19]=[C:15]3[N:14]=[C:13](Cl)[C:12]=2[CH3:27])[C@H:7]([OH:28])[C@@H:6]1[OH:29])[NH2:2]>[Pd].O1CCCC1>[S:1](=[O:31])(=[O:30])([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][CH:21]=4)[CH:19]=[C:15]3[N:14]=[CH:13][C:12]=2[CH3:27])[C@H:7]([OH:28])[C@@H:6]1[OH:29])[NH2:2]

Participants

4

Reactant 1

HCID 89758788HCID 89758788, compound

Product 1

HCID 71715656HCID 71715656, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A pressure bottle is charged with (rac)-{(1R,2R,3S,4R)-4-[(5-chloro-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)amino]-2,3-dihydroxycyclopentyl}methyl rel-sulfamate (111 mg, 0.237 mmol), tetrahydrofuran (1.4 mL) and Pd [10% on carbon/50% water wet; Degussa type) 76 mg, 0.036 mmol)]. The reaction is stirred at room temperature under an atmosphere of hydrogen (30 psi) for 18 hr. The reaction mixture is filtered through celite and concentrated in vacuo. The crude material is purified by preparative HPLC to provide (rac)-{(1R,2R,3S,4R)-2,3-dihydroxy-4-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)amino]cyclopentyl}methyl rel-sulfamate (15 mg, yield 13%). LCMS: (FA) M+1 434; 1H NMR (400 MHz, MeOD) δ 8.05-7.98 (m, 2H), 7.94 (s, 1H), 7.43 (t, J=7.4 Hz, 2H), 7.36 (t, J=7.3 Hz, 1H), 6.69 (s, 1H), 4.20 (t, J=7.8 Hz, 2H), 4.03-3.94 (m, 2H), 2.64 (s, 1H), 2.54-2.31 (m, 5H), 1.64-1.51 (m, 1H).

Workup

  1. filtrationThe reaction mixture is filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude material is purified by preparative HPLC

Sources & evidence

ORD record
ord-1d3e6bd78eee439382550b7035f22c68
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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