Triethylamine → trans-N-[2,3,4,14b-Tetrahydro-7-[(1-oxopropyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]-2,2,2-trifluoroacetamide

HRID 16180Notes

Reaction equation

HRID 16180 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[C:28](Cl)(=[O:31])[CH2:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl>[O:31]=[C:28]([NH:1][C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1)[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 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-trifluoroacetamide

Product 1

HCID 86599891trans-N-[2,3,4,14b-Tetrahydro-7-[(1-oxopropyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]-2,2,2-trifluoroacetamideYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 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 (50 mg, 0.13 mmol) in CH2Cl2 (2 mL) was added propionyl chloride (11 μl, 0.13 mmol) and triethylamine (20 μl, 0.14 mmol). The reaction mixture was stirred for 1.5 h at room temperature. The reaction mixture was quenched with sat. NaHCO3 (aq) and extracted with CH2Cl2. The organic layer was dried and evaporated. The crude product was purified on silica and by HPLC to afford the title compound (27 mg, 48%). Data (m/z)=434 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 (aq)
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe crude product was purified on silica and by HPLC

Sources & evidence

ORD record
ord-8e1b4e41797d4bbab8b5424b4c3a5404
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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