Hydrochloric Acid → trans-N-(7-Amino-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16179Notes

Reaction equation

HRID 16179 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([NH:5][C@H:6]1[C@@H:16]2[N:10]([C:11]3[CH:24]=[C:23]([NH:25]CC4C=CC=CC=4)[CH:22]=[CH:21][C:12]=3[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=32)[CH2:9][CH2:8][CH2:7]1)=[O:4].Cl.O1CCOCC1>C(O)C.[Pd]>[NH2:25][C:23]1[CH:22]=[CH:21][C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[C@@H:16]3[C@H:6]([NH:5][C:3](=[O:4])[C:2]([F:33])([F:34])[F:1])[CH2:7][CH2:8][CH2:9][N:10]3[C:11]=2[CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86599889trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide

Product 1

HCID 86599890trans-N-(7-Amino-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide (944 mg, 2.0 mmol) in ethanol (16 mL) were added Pd/C 10% (111 mg) and a solution of 4M HCl in dioxane (778 μl, 3.11 mmol). The resulting reaction mixture was hydrogenated at 3 bar for 6 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with ethanol. After filtration through dicalite and thorough washing with ethyl acetate, the volatiles were removed in vacuo. A part of the crude product was purified with HPLC to afford the title compound (29 mg, 53%). Data (m/z)=378 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was quenched with sat. NaHCO3 (aq)
  3. additiondiluted with ethanol
  4. filtrationAfter filtration through dicalite
  5. washthorough washing with ethyl acetate
  6. customthe volatiles were removed in vacuo
  7. customA part of the crude product was purified with HPLC

Sources & evidence

ORD record
ord-62780275474946fcb37d7b069485186d
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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