Cyclohexyl isocyanate → 3-[2-(trifluoromethyl)-4'-fluorobenzhydryloxy]-N-(cyclohexyl)-azetidine-1-carboxamide

HRID 1785711Notes

Reaction equation

HRID 1785711 reaction equation
Cl.[F:2][C:3]([F:24])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][NH:17][CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[CH:29]1([N:35]=[C:36]=[O:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[F:24][C:3]([F:2])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][N:17]([C:36]([NH:35][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:37])[CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 19660Carbonate IonHCID 689056553-[2-(Trifluoromethyl)-4'-fluorobenzhydryloxy]azetidine hydrochloride

Product 1

HCID 112823613-[2-(trifluoromethyl)-4'-fluorobenzhydryloxy]-N-(cyclohexyl)-azetidine-1-carboxamideYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (200 mg, 0.55 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.01 mmol/g; 550 mg, 1.65 mmol) and cyclohexyl isocyanate (72 μL, 0.55 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which time it was poured onto a DCM-wetted SCX-2 (1 g) cartridge. The sample was eluted with DCM (16 mL), then evaporated to afford the desired product as a colourless glass (194 mg, 78%).

Workup

  1. washThe sample was eluted with DCM (16 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-95fd3190ab70495497f761ac3b49cfda
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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