Hydrochloric Acid → HCID 178525330, compound

HRID 2289975Notes

Reaction equation

HRID 2289975 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl>CN(C=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 178525329HCID 178525329, compound

Product 1

HCID 178525330HCID 178525330, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of the title compound of Example 113 (0.250 g) and triethylamine (0.09 mL) in 100 mL of 3:1 CH2Cl2MeOH is added 10% Pd/C (0.050 g). The mixture is hydrogenated at 30 psi H2 for 6 h. The reaction is filtered through celite and the filtrate is condensed. The crude product is dissolved in DMF (~25 mL) and acidified with 1 N HCl (25 mL). The resulting solid is collected, dried and recrystallized from EtOH to yield 0.152 g of the desired product as a white solid.

Workup

  1. filtrationThe reaction is filtered through celite
  2. customcondensed
  3. customThe resulting solid is collected
  4. customdried
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-a79a98e4cb1249258493ef1fb6df8be0
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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