Ethylamine → HCID 57344515, compound

HRID 2401364Notes

Reaction equation

HRID 2401364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3=[C:19]([CH3:22])[O:20][N:21]=[C:11]3[C@H:10]([CH2:23][C:24](OC(C)(C)C)=[O:25])[N:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[CH2:38]([NH2:40])[CH3:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3=[C:19]([CH3:22])[O:20][N:21]=[C:11]3[C@H:10]([CH2:23][C:24]([NH:40][CH2:38][CH3:39])=[O:25])[N:9]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57344514HCID 57344514, compound

Product 1

HCID 57344515HCID 57344515, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added tert-butyl 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,3-e]azepin-4-yl)acetate (0.059 g, 0.140 mmol), CH2Cl2 (2 mL), and TFA (0.400 mL, 5.19 mmol). The reaction was stirred at room temperature for 2 h before concentrating. The crude residue was dried for 30 min before addition of DMF (2 mL), ethylamine (0.098 mL, 0.195 mmol, 2M in THF), HATU (0.080 g, 0.209 mmol), and Hunig's Base (0.073 mL, 0.419 mmol). The reaction was stirred at room temperature for 1 h before diluting with water and extracting with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,3-e]azepin-4-yl)-N-ethylacetamide (0.022 g, 0.056 mmol). 1H NMR (500 MHz, Acetone-d6) δ 7.76-7.72 (m, 1H), 7.71-7.66 (m, 1H), 7.49-7.42 (m, 3H), 7.41-7.36 (m, 3H), 7.32 (br. s, 1H), 4.62 (dd, J=5.4, 8.3 Hz, 1H), 3.35-3.21 (m, 2H), 3.20-3.09 (m, 2H), 2.67 (s, 3H), 1.14 (t, J=7.3 Hz, 3H); LC/MS m/z 394.

Workup

  1. concentrationbefore concentrating
  2. stirringThe reaction was stirred at room temperature for 1 h
  3. extractionextracting with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-a8b94496424f464f94484a678a234383
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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