Hydrochloric Acid → HCID 135592794, compound

HRID 1937394Notes

Reaction equation

HRID 1937394 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:16]([NH2:17])=[C:15]([C:18](=O)[CH2:19]C)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.Cl.C([OH:25])C>[Pd]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:16]3[NH:17][C:19]([OH:25])=[CH:18][C:15]=3[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69963857HCID 69963857, compound

Product 1

HCID 135592794HCID 135592794, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4-(6-Chloro-2,3-dihydro-indol-1-yl)-5-amino-6-methylacetylpyrimidine (541 mg, 1.55 mmol) in 40 mL of ethanol was added 25 mol % of 10% palladium on carbon (125 mg) and 0.11 mL of 1N HCl (1.55 mmol). The reaction mixture was hydrogenated for 3 hours at 50 psi. The reaction mixture was filtered through Celite and concentrated in vacuo. The brown residue was slurried in methanol and the white solid title product was filtered off (279 mg, 63%)LC-MS=287 (M+), RP18-HPLC RT: 5.61 min. MP: 250° C.(dec).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. filtrationthe white solid title product was filtered off (279 mg, 63%)

Sources & evidence

ORD record
ord-b84ed45e5be44ae7a8ecc1ce6bc4fc0f
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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