Triethylamine → HCID 67050780, compound

HRID 1498526Notes

Reaction equation

HRID 1498526 reaction equation
FC(F)(F)S(O[C:7]1[N:29]=[CH:28][C:10]2[C:11]3[N:12]([CH:16]=[C:17]([C:19]4[N:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[C:21]([CH3:27])[N:20]=4)[N:18]=3)[CH2:13][CH2:14][O:15][C:9]=2[CH:8]=1)(=O)=O.[CH2:32]([NH2:43])[C:33]1[CH:42]=[CH:41][C:38]([O:39][CH3:40])=[C:35]([O:36][CH3:37])[CH:34]=1.C(N(CC)CC)C>CN1CCCC1=O.O.CO.C(Cl)Cl>[CH3:37][O:36][C:35]1[CH:34]=[C:33]([CH:42]=[CH:41][C:38]=1[O:39][CH3:40])[CH2:32][NH:43][C:7]1[N:29]=[CH:28][C:10]2[C:11]3[N:12]([CH:16]=[C:17]([C:19]4[N:23]([CH:24]([CH3:25])[CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=4)[N:18]=3)[CH2:13][CH2:14][O:15][C:9]=2[CH:8]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 79832VeratrylamineHCID 58204573trifluoro-methanesulphonic acid 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yl ester

Product 1

HCID 67050780HCID 67050780, compoundYield 23.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl trifluoromethanesulfonate (790 mg, 1.7 mmol) was dissolved in N-methylpyrrolidinone (11 mL) and treated with veratrylamine (1.0 mL, 6.9 mmol) and triethylamine (1.9 mL, 14 mmol). The reaction mixture was heated at 120° C. overnight. The mixture was diluted with water and 20% MeOH in DCM and the layers separated. The aqueous phase was extracted into DCM/MeOH (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford N-(3,4-dimethoxybenzyl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-amine as a light yellow solid (190 mg, 23%). 1H NMR (400 MHz, DMSO) δ 8.99 (s, 1H), 7.75 (s, 1H), 6.95 (d, J=1.5 Hz, 1H), 6.92 (s, 1H), 6.88 (s, 1H), 6.02 (s, 1H), 5.85 (hept, J=6.6 Hz, 1H), 4.65 (s, 1H), 4.50-4.36 (m, 6H), 3.73 (s, 6H), 2.24 (s, 3H), 1.44 (d, J=6.6 Hz, 6H)

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted into DCM/MeOH (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customabsorbed onto celite for purification by flash chromatography

Sources & evidence

ORD record
ord-387215df4e48417e9ea8b3daecd4a4d6
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

Loading…