Methanol → HCID 22485555, compound

HRID 2181342Notes

Reaction equation

HRID 2181342 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([CH2:32][CH2:33][N:34]([CH3:62])[CH2:35][CH2:36][C:37](=O)[NH:38][C:39]3[CH:40]=[CH:41][C:42]([C:45]4[CH:50]=[C:49]([O:51][CH3:52])[C:48]([O:53][CH2:54][C:55]([F:58])([F:57])[F:56])=[C:47]([O:59][CH3:60])[CH:46]=4)=[N:43][CH:44]=3)=O)=[CH:25][N:24]=2)[CH:12]=[C:13]([O:21][CH3:22])[C:14]=1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18].CO>O1CCCC1>[CH3:52][O:51][C:49]1[CH:50]=[C:45]([C:42]2[CH:41]=[CH:40][C:39]([NH:38][CH2:37][CH2:36][CH2:35][N:34]([CH3:62])[CH2:33][CH2:32][CH2:30][NH:29][C:26]3[CH:27]=[CH:28][C:23]([C:11]4[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[C:9]([O:8][CH3:7])[CH:10]=4)=[N:24][CH:25]=3)=[CH:44][N:43]=2)[CH:46]=[C:47]([O:59][CH3:60])[C:48]=1[O:53][CH2:54][C:55]([F:56])([F:57])[F:58]

Participants

5

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 22485532HCID 22485532, compound

Product 1

HCID 22485555HCID 22485555, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Under nitrogen, lithium aluminum hydride (4.28 g, 113 mmol) was added to an ice-cold solution of N,N-bis[2-[N-[2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]-5-pyridyl]carbamoyl]ethyl]methylamine (22.50 g, 28.3 mmol) in anhydrous tetrahydrofuran (500 mL). The ice bath was removed, and the reaction mixture was stirred at 65° C. for 1 hour. Methanol (20 mL, 490 mmol) was added to the ice-cold reaction mixture, and the ice bath was removed. Water (20 mL), diethyl ether (2 L), and anhydrous magnesium sulfate (130 g) were added, and the mixture was stirred overnight at room temperature. Insoluble materials were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide N,N-bis[N-[2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]-5-pyridyl]-3′-aminopropyl]methylamine as a colorless oil (20.32 mg, yield: 94%).

Workup

  1. customThe ice bath was removed
  2. customthe ice bath was removed
  3. additionWater (20 mL), diethyl ether (2 L), and anhydrous magnesium sulfate (130 g) were added
  4. stirringthe mixture was stirred overnight at room temperature
  5. customInsoluble materials were removed by filtration through Celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2b483e4bb9b043b0861c97bcafbd5d2e
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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