Hydrochloric Acid → HCID 22632211, compound

HRID 2416718Notes

Reaction equation

HRID 2416718 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:28]=[CH:27][C:15]2[CH2:16][CH:17]([CH2:22][C:23]([O:25]C)=[O:24])[C:18](=[O:21])[NH:19][CH2:20][C:14]=2[CH:13]=1.Cl.O1CCOCC1.[H][H]>[Pd].CO>[NH:3]1[CH2:4][CH2:5][CH2:6][N:1]=[C:2]1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:28]=[CH:27][C:15]2[CH2:16][CH:17]([CH2:22][C:23]([OH:25])=[O:24])[C:18](=[O:21])[NH:19][CH2:20][C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 53634998HCID 53634998, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22632211HCID 22632211, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (±)-8-[3-(pyrimidin-2-ylamino)-1-propyloxy]-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.36 g, 0.94 mmol), 4 M HCl in dioxane (0.25 mL, 1 mmol), 10% palladium on charcoal (0.24 g, 0.24 mmol), and MeOH (5 mL) was stirred under a balloon of hydrogen. After 18 hr, the mixture was filtered and the filtrate was concentrated. The residue was partitioned between EtOAc and aqueous K2CO3. A solid precipitated, which was collected by filtration and dried to give the title compound as a white solid: MS m/e 375.4 (M+H)+. Anal. Calcd for C19H26N4O4.2.5 H2O: C, 54.40; H, 7.45; N, 13.35. Found: C, 54.68; H, 7.12; N, 13.39.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between EtOAc and aqueous K2CO3
  4. customA solid precipitated
  5. filtrationwhich was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-0371c3c69efe48069cbe0796d246acca
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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