Triethylamine → N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)urea

HRID 1592339Notes

Reaction equation

HRID 1592339 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:20])[CH:16]=2)[CH2:11]1.C1([O:27][C:28](=O)[NH:29][C:30]2[CH:35]=[C:34]([C:36]3[N:40]([CH3:41])[N:39]=[N:38][N:37]=3)[CH:33]=[C:32]([CH2:42][CH3:43])[CH:31]=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH2:42]([C:32]1[CH:31]=[C:30]([NH:29][C:28]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[CH2:8][NH:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:20])[CH:16]=3)[CH2:11]2)=[O:27])[CH:35]=[C:34]([C:36]2[N:40]([CH3:41])[N:39]=[N:38][N:37]=2)[CH:33]=1)[CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69423061N-{[(1S,2R)-2-aminocyclohexyl]methyl}-(2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 11752488N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)ureaYield 45.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-{[(1S,2R)-2-aminocyclohexyl]methyl}-(2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-amine (60 mg, 217 μmol) and phenyl[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]carbamate (54 mg, 217 μmol) in acetonitrile (2 mL) was treated with triethylamine (75 μL, 540 μmol). After being stirred at room temperature for 18 hours, the mixture was concentrated under vacuum. The residue was purified by flash column chromatography, eluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonia, to provide an amorphous solid (50 mg, 45%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was purified by flash column chromatography
  3. washeluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonia

Sources & evidence

ORD record
ord-737d17c08a5348a280ddcbd8bee30d7a
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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