HCID 86727378, compound → HCID 76287822, compound

HRID 519063Notes

Reaction equation

HRID 519063 reaction equation
C([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:41])[C:25](=[O:40])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CO.Cl.[OH-].[OH-].[Pd+2]>[CH3:41][CH:24]1[N:23]2[C:28]([CH2:29][O:30][C:31]3[C:22]2=[CH:21][C:20]([NH:19][C:16]2([CH3:18])[CH2:17][NH:14][CH2:15]2)=[C:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:32]=3)=[N:27][NH:26][C:25]1=[O:40]

Participants

6

Reactant 1

HCID 86727378HCID 86727378, compound

Product 1

HCID 76287822HCID 76287822, compoundYield 139.8%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-7-phenyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Example #79, Step C, 0.10 g, 0.18 mmol) in THF (20 mL), MeOH (20 mL) and aqueous HCl (12N, 0.3 mL) was added Pd(OH)2/C (10%, 0.02 g, 0.014 mmol) and the solution was heated at 50° C. under an atmosphere of H2 (55 psi) for 4 h. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was evaporated in vacuo to give 4-methyl-6-(3-methyl-azetidin-3-ylamino)-7-phenyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.095 g, 57% pure, 82%), which was used in the next step directly without further purification. LC/MS (Table 1, Method 2) Rt=0.890 min; MS m/z: 378 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-410bc7a303964d77ac4eebd9a71d08c8
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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