Ammonium Chloride → HCID 86599884, compound

HRID 16173Notes

Reaction equation

HRID 16173 reaction equation
Br[C:2]1[C:12]2[N:11]3[CH2:13][CH2:14][CH2:15][C@@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C@H:10]3[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:28][O-:29].[Na+].[NH4+].[Cl-]>CN(C=O)C.CO.[Cu]I>[CH3:28][O:29][C:2]1[C:12]2[N:11]3[CH2:13][CH2:14][CH2:15][C@@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C@H:10]3[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 86599881trans-N-(6-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido-[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86599884HCID 86599884, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Copper(I) iodide (21 mg, 0.11 mmol) was added to a stirring solution of trans-N-(6-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (100 mg, 0.22 mmol) in DMF (1.5 mL) in a Dean-Stark apparatus. Subsequently a solution of NaOMe (1.2 mL, 1.2 mmol) in methanol was added and stirring was continued at 135° C. for 4 h. After cooling down, the reaction mixture was poured into sat (aq) NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. After purification on a SPE-column and by HPLC the title compound (11 mg, 13%) was obtained. Data: 1H-NMR (400 MHz, CDCl3) 1.50 (m, 1H), 1.76 (m, 1H), 1.87 (m, 1H), 1.94 (m, 1H), 2.87 (m, 1H), 3.29 (dt, J=12, 3.2, 1H), 3.86 (s, 3H), 4.28 (d, J=3.2, 1H), 4.81 (m, 1H), (Ar) 6.66 (d, J=12, 1H), 6.78 (d, J=12, 1H), 7.10 (m, 1H), 7.20-7.31 (m, 4H), 8.18 (m, 1H, NH).

Workup

  1. temperatureAfter cooling down
  2. additionthe reaction mixture was poured
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customAfter purification on a SPE-column and by HPLC the title compound (11 mg, 13%)
  8. customwas obtained

Sources & evidence

ORD record
ord-b958e7680711407db1921dab8c21de85
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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