Methylamine → 6-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine

HRID 2401375Notes

Reaction equation

HRID 2401375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15](F)=[N:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:20]([CH3:23])=[N:21][O:22][C:11]=3[CH2:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:24][NH2:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([NH:25][CH3:24])=[N:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:20]([CH3:23])=[N:21][O:22][C:11]=3[CH2:10][N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 573445176-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine

Product 1

HCID 573445216-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine

Conditions

Temperature
80 °C

Procedure

To 6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine (0.020 g, 0.061 mmol) was added a solution of methylamine (33% in EtOH) (4 mL) at room temperature. The reaction was heated to 80° C. for 22 h before silica gel was added. The solvent was removed under vacuum, the dry silica gel was packed and the adsorbed product was purified by flash chromatography (hexane/EtOAc 8:2 to 2:8) to give 6-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine as a white solid (0.014 g). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (d, J=5.26 Hz, 1H), 7.35 (td, J=2.30, 8.93 Hz, 2H), 7.30 (td, J=2.30, 8.93 Hz, 2H), 6.93 (d, J=5.26 Hz, 1H), 5.87 (q, J=4.35 Hz, 1H), 5.22 (d, J=12.82 Hz, 1H), 4.03 (s, 1H), 2.61 (d, J=4.58 Hz, 3H), 2.50 (s, 3H); LC/MS m/z 339 [M+H]+.

Workup

  1. additionwas added
  2. customThe solvent was removed under vacuum
  3. customthe adsorbed product was purified by flash chromatography (hexane/EtOAc 8:2 to 2:8)

Sources & evidence

ORD record
ord-09e3555359fd4e2e99700ded1e7d00fe
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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