HCID 10990514, compound → HCID 21833021, compound

HRID 1740754Notes

Reaction equation

HRID 1740754 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[C:12]3[NH:18][CH2:17][CH2:16][CH2:15][C:13]3=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1.C[Al](C)C.[CH3:24][C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[CH:27][C:26]=1[C:37]1[CH:42]=[CH:41][C:40]([C:43](OC)=[O:44])=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.ClCCl>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[C:12]3[N:18]([C:43]([C:40]4[CH:39]=[CH:38][C:37]([C:26]5[CH:27]=[CH:28][C:29]([N:31]6[CH2:35][CH2:34][CH2:33][C:32]6=[O:36])=[CH:30][C:25]=5[CH3:24])=[CH:42][CH:41]=4)=[O:44])[CH2:17][CH2:16][CH2:15][C:13]3=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 10990514HCID 10990514, compoundHCID 10999839HCID 10999839, compoundHCID 16682925Trimethylaluminum2×

Product 1

HCID 21833021HCID 21833021, compoundYield 6.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
82.5 °C

Procedure

A stirred solution of 4-(2-dimethylaminoethyl)-2,3,6,7,8,9-hexahydro-4H-pyrido[2,3-g][1,4]benzoxazine (D5, 130 mg, 0.49 mmole) in toluene (4 ml) under argon was treated with trimethylaluminium (0.27 ml of 2M in toluene, 0.54 mmole) and stirred for 20 mins. Methyl 2'-methyl4'-(2-oxo-1-pyrrolidinyl)biphenyl-4-carboxylate (D29, 154 mg, 0.50 mmole) was added and the mixture heated at 80-85° C. for 6 h, then further trimethylaluminium (0.45 ml) was added and the mixture heated under reflux for 6 h. The reaction mixture was allowed to cool, poured into a slurry of silica gel (4 g) in dichioromethane (10 ml), then loaded onto a chromatography column and eluted with 0-16% methanol/dichloromethane. The product obtained was further purified by prep. plate TLC on silica gel eluting with 10% methanol/dichloromethane to afford the title compound as a light green semi-solid (16 mg). This was converted to it hydrochloride salt as a pale yellow solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 6 h
  3. temperatureto cool
  4. washeluted with 0-16% methanol/dichloromethane
  5. customThe product obtained
  6. customwas further purified by prep

Sources & evidence

ORD record
ord-d5f309bd1ba2456499b0ba7f29fdc377
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

Loading…