Hydrochloric Acid → (R)-4-methyl-6-(3-methyl-azetidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519239Notes

Reaction equation

HRID 519239 reaction equation
C([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][CH:33]=2)[O:30][CH2:29][C:28]2[N:23]3[C@H:24]([CH3:35])[C:25](=[O:34])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>CO>[CH3:35][C@H: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])[CH2:15][NH:14][CH2:17]2)=[CH:33][CH:32]=3)=[N:27][NH:26][C:25]1=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86727521(R)-6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Product 1

HCID 86727638(R)-4-methyl-6-(3-methyl-azetidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-oneYield 139.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (R)-6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Example #148, Step E, 20 g, 42.8 mmol) and PdOH2/C(10%, 10 g, 71.2 mmol) in MeOH (400 mL) and HCl (2 mL) was stirred at 50° C. under H2 (50 psi) for 48 h. The reaction mixture was cooled to ambient temperature and filtered, washed with hot MeOH (3×100 mL). The combined filtrate was concentrated in vacuo to give (R)-4-methyl-6-(3-methyl-azetidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (18 g, 99%), which was used directly. LC/MS (Table 1, Method 25) Rt=0.525 min.; MS m/z: 302 [M+H]+.

Workup

  1. filtrationfiltered
  2. washwashed with hot MeOH (3×100 mL)
  3. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-aea77a74641940c78d1642cba981c755
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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