HCID 117942664, compound → HCID 117951888, compound

HRID 1499282Notes

Reaction equation

HRID 1499282 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:34][CH2:33][C:11]3([CH2:15][N:14](C(OCC4C=CC=CC=4)=O)[C@H:13]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:35][C@H:36]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=2[N:48]2[CH:52]=[CH:51][C:50]([CH3:53])=[N:49]2)[C:37]([F:40])([F:39])[F:38])[N:3]=1>CCOC(C)=O.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:34][CH2:33][C:11]3([CH2:15][NH:14][C@H:13]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:35][C@H:36]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=2[N:48]2[CH:52]=[CH:51][C:50]([CH3:53])=[N:49]2)[C:37]([F:38])([F:40])[F:39])[N:3]=1

Participants

4

Reactant 1

HCID 117942664HCID 117942664, compound

Product 1

HCID 117951888HCID 117951888, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-benzyl 3-tert-butyl 8-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (1.35 g, 1.7 mmol) in EtOAc (130 mL) was added 5% (w/w) Pd/C (130 mg). The solution was degassed, charged with 1 atm H2 (balloon), and stirred at RT for 3.5 h. Then the solids were filtered through celite, washed with EtOAc/methanol, and the filtrate was concentrated in vacuo. Purification on a 220 g Isco RediSep silica cartridge (CH2Cl2/MeOH/NH4OH) provided the title compound as an off-white solid.

Workup

  1. customThe solution was degassed
  2. additioncharged with 1 atm H2 (balloon)
  3. filtrationThen the solids were filtered through celite
  4. washwashed with EtOAc/methanol
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification on a 220 g Isco RediSep silica cartridge (CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-fedb653c518342ff9c106aaca78c04d3
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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