HCID 90039259, compound → HCID 90037993, compound

HRID 1055396Notes

Reaction equation

HRID 1055396 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][C:13]2[C:21]([F:26])=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[NH:11][C:10]1=[O:27])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[NH2:8][CH:9]1[C:15]2([CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[O:14][C:13]2[C:21]([F:26])=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[NH:11][C:10]1=[O:27]

Participants

4

Reactant 1

HCID 90039259HCID 90039259, compound

Product 1

HCID 90037993HCID 90037993, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

3-(Dibenzylamino)-8,9-difluoro-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-4(5H)-one (100 mg, 215 μmol, Eq: 1.00) was added to MeOH (10 mL) and the mixture warmed 40° C. to give a light yellow suspension. 20% Pd(OH)2/C (100 mg, 215 μmol, Eq: 1.00) was added, the mixture was degassed and stirred at RT under H2 for 6.5 h. The mixture was filtered through Celite and concentrated under reduced pressure to afford 3-amino-8,9-difluoro-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-4(5 h)-one (60 mg, 98% yield) as colorless oil which was used without purification. MS m/z 285.0 (MH+)

Workup

  1. customto give a light yellow suspension
  2. customthe mixture was degassed
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47085b71a67e441688c276ba5720f518
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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