HCID 136342493, compound → HCID 136342435, compound

HRID 1611192Notes

Reaction equation

HRID 1611192 reaction equation
[ClH:1].[NH2:2][C@@H:3]([C:11]1[C:20]2[CH2:19]OC(=O)[NH:16][C:15]=2[N:14]=[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[CH:12]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(#N)C>[ClH:1].[NH2:16][C:15]1[N:14]=[C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[CH:12]=[C:11]2[C@@H:3]([CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][CH2:19][C:20]=12

Participants

3

Reactant 1

HCID 136342493HCID 136342493, compound

Product 1

HCID 136342435HCID 136342435, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-[(1R)-1-amino-2-phenylethyl]-7-(2-hydroxyphenyl)-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazin-2-one hydrochloride (0.014 g, 0.035 mmol), which was obtained in Example 18-4, in acetonitrile (3.0 mL) was heated at reflux for 2 hrs. The resulting mixture was concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (1.0 mL), treated with 4N HCl solution in 1,4-dioxane (0.5 mL), and concentrated under reduced pressure. The residue was triturated with acetonitrile, and dried under reduced pressure to give 2-[(1R)-4-amino-1-benzyl-2,3-dihydro-1H-pyrrolo[3,4-d]pyridin-6-yl]phenol hydrochloride as a white solid (0.010 g, yield; 80%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in 1,4-dioxane (1.0 mL)
  5. additiontreated with 4N HCl solution in 1,4-dioxane (0.5 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with acetonitrile
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e8cc4cee1bb5406eb5d284fb6ea32b35
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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