3,5-Bis(trifluoromethyl)phenyl isocyanate → 3-(3,5-bis(trifluoromethyl)phenyl)-1-(4-tert-butylcyclohexyl)-1-[4-(2-2H-tetrazol-5-yl-acetyl)-benzyl]urea

HRID 480381Notes

Reaction equation

HRID 480381 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:31])[CH2:20][C:21]3[N:22]=[N:23][N:24](C(OC)(C)C)[N:25]=3)=[CH:15][CH:14]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[F:32][C:33]([F:48])([F:47])[C:34]1[CH:35]=[C:36]([N:44]=[C:45]=[O:46])[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1>C1COCC1>[F:32][C:33]([F:47])([F:48])[C:34]1[CH:35]=[C:36]([NH:44][C:45](=[O:46])[N:11]([CH:8]2[CH2:9][CH2:10][CH:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:6][CH2:7]2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:31])[CH2:20][C:21]3[N:25]=[N:24][NH:23][N:22]=3)=[CH:15][CH:14]=2)[CH:37]=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:39]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 187688831-{4-[(4-Tert-butylcyclohexylamino)methyl]phenyl}-2-[2-(1-methoxy-1-methylethyl)-2h-tetrazol-5-yl]ethanone

Product 1

HCID 187688993-(3,5-bis(trifluoromethyl)phenyl)-1-(4-tert-butylcyclohexyl)-1-[4-(2-2H-tetrazol-5-yl-acetyl)-benzyl]ureaYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{4-[(4-tert-Butylcyclohexylamino)methyl]phenyl}- 2-[2-(1-methoxy-1-methylethyl)-2H-tetrazol-5-yl]ethanone (320 mg, 0.75 mmol) was dissolved in THF (5 ml), and 3,5-bis(trifluoromethyl)phenyl isocyanate (191 mg, 0.75 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then taken to dryness by rotary evaporation. The residue was stripped twice from acetonitrile to give 450 mg (88%) of title material.

Workup

  1. customtaken to dryness by rotary evaporation

Sources & evidence

ORD record
ord-8cb3ed5d3a3146f1b471035ff8b254b5
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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