HCID 86727361, compound → HCID 86727362, compound

HRID 519005Notes

Reaction equation

HRID 519005 reaction equation
[CH:1]([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]([F:37])([F:36])[F:35])[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:47])[C:25](=[O:46])[N:26](COCC[Si](C)(C)C)[N:27]=2)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:1]([N:14]1[CH2:15][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2[C:34]([F:37])([F:36])[F:35])[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:47])[C:25](=[O:46])[NH:26][N:27]=2)([CH3:18])[CH2:17]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86727361HCID 86727361, compound

Product 1

HCID 86727362HCID 86727362, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.020 g, 0.034 mmol) in DCM (0.5 mL) and TFA (0.25 mL) was stirred at ambient temperature for 1 h. The solvent was removed in vacuo. The residue was dissolved in THF (0.5 mL) and aqueous ammonium hydroxide solution (25%, 0.25 mL) was added. The mixture was stirred for additional 2 h at ambient temperature. The mixture was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo to give crude 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one as a yellow solid (0.015 g, 84%), which was used in next step directly. LC/MS (Table 1, Method 2) Rt=0.997 min.; MS m/z: 536 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in THF (0.5 mL)
  3. additionaqueous ammonium hydroxide solution (25%, 0.25 mL) was added
  4. additionThe mixture was diluted with water (10 mL)
  5. extractionextracted with EtOAc (3×10 mL)
  6. washThe combined organic phase was washed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6f5c82af333c40a08d9c507fe8b33de0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…