4-Methylmorpholine → 4-(5-{[(2S)-2-(Trifluoromethyl)-1-pyrrolidinyl]methyl}-1H-tetrazol-1-yl)benzonitrile

HRID 517779Notes

Reaction equation

HRID 517779 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1.CN1CCOCC1.[F:23][C:24]([F:31])([F:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1>C(#N)C>[F:23][C:24]([F:31])([F:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2782840(2S)-2-(trifluoromethyl)pyrrolidineHCID 666554054-[5-(chloromethyl)-1H-tetrazol-1-yl]benzonitrile2×

Product 1

HCID 866918964-(5-{[(2S)-2-(Trifluoromethyl)-1-pyrrolidinyl]methyl}-1H-tetrazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of 4-[5-(chloromethyl)-1H-tetrazol-1-yl]benzonitrile (100 mg, 0.455 mmol, Intermediate 10) and polymer supported N-methylmorpholine (4 mmol/g, 171 mg, 0.683 mmol) in acetonitrile (3 mL) was added (2S)-2-(trifluoromethyl)pyrrolidine (95 mg, 0.683 mmol). The reaction mixture was heated at 120° C. for 20 min in a microwave reactor and at 140° C. for 20 min and at 150° C. for 30 min and finally at 160° C. for 30 min in the microwave reactor.

Sources & evidence

ORD record
ord-1a797e468ec042b387ac8b237e5163cf
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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