Cyclohexyl isocyanate → 3-[2-(trifluoromethyl)-4'-(methylthio)benzhydryloxy]-N-(cyclo-hexyl)azetidine-1-carboxamide

HRID 1785714Notes

Reaction equation

HRID 1785714 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH:6]([O:15][CH:16]1[CH2:19][NH:18][CH2:17]1)[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[CH:30]1([N:36]=[C:37]=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[F:25][C:3]([F:2])([F:24])[C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH:6]([O:15][CH:16]1[CH2:19][N:18]([C:37]([NH:36][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:38])[CH2:17]1)[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 19660Carbonate IonHCID 689042363-[2-Trifluoromethyl-4'-(methylthio)benzhydryloxy]azetidine hydrochloride

Product 1

HCID 112829863-[2-(trifluoromethyl)-4'-(methylthio)benzhydryloxy]-N-(cyclo-hexyl)azetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (100 mg, 0.26 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.10 mmol/g; 250 mg, 0.84 mmol) and cyclohexyl isocyanate (33 μL, 0.26 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 (18 mL), then evaporated to afford the desired product as a white, crystalline solid (65 mg, 52%).

Workup

  1. washThe sample was eluted with DCM (18 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-b882c3fe42704152805daba2a81e1922
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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