HCID 137010196, compound → HCID 137010190, compound

HRID 2205179Notes

Reaction equation

HRID 2205179 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[N:6]=[CH:7][N:8]([C@H:11]3[C@H:15]([OH:16])[C@H:14]([O:17]CC4C=CC=CC=4)[C@:13]([CH2:28][O:29]CC4C=CC=CC=4)([CH:25]([F:27])[F:26])[O:12]3)[C:9]=2[N:10]=1>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[NH:3][C:4](=[O:37])[C:5]2[N:6]=[CH:7][N:8]([C@H:11]3[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@:13]([CH:25]([F:27])[F:26])([CH2:28][OH:29])[O:12]3)[C:9]=2[N:10]=1

Participants

4

Reactant 1

HCID 137010196HCID 137010196, compound

Product 1

HCID 137010190HCID 137010190, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 22 (0.22 g, 0.42 mmol) in methanol (30 mL) was added HCO2NH4 (600 mg, 9.52 mmol), followed by Pd(OH)2/C (500 mg). The reaction mixture was stirred at 80° C. for 15 h, then cooled to 25° C., filtered and then evaporated to dryness under reduced pressure. Purification by silica gel chromatography [dichloromethane:methanol (20:1 to 5:1)] and prep-HPLC provided the product 23 (0.046 g, 33%) as a white solid. LC-MS (M+H)+=334.1

Workup

  1. temperaturecooled to 25° C.
  2. filtrationfiltered
  3. customevaporated to dryness under reduced pressure
  4. customPurification by silica gel chromatography [dichloromethane:methanol (20:1 to 5:1)]

Sources & evidence

ORD record
ord-5ed30586acfd4d57b10a11233ee980e3
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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