phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate → N-{(1R,2S)-3-[[3-(4-fluorophenyl)propyl](methyl)amino]-2-hydroxy-1-methylpropyl}-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea

HRID 1592365Notes

Reaction equation

HRID 1592365 reaction equation
[NH2:1][C@H:2]([CH3:18])[C@@H:3]([OH:17])[CH2:4][N:5]([CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:6].[CH3:19][N:20]1[C:24]([C:25]2[CH:26]=[C:27]([NH:31][C:32](=O)[O:33]C3C=CC=CC=3)[CH:28]=[CH:29][CH:30]=2)=[N:23][N:22]=[N:21]1>C(#N)C>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][N:5]([CH3:6])[CH2:4][C@H:3]([OH:17])[C@H:2]([NH:1][C:32]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]3[N:20]([CH3:19])[N:21]=[N:22][N:23]=3)[CH:26]=2)=[O:33])[CH3:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 58997707(2S,3R)-3-amino-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-ol

Product 1

HCID 44447135N-{(1R,2S)-3-[[3-(4-fluorophenyl)propyl](methyl)amino]-2-hydroxy-1-methylpropyl}-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]ureaYield 3.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of Step g (186 mg, 7.3 mmol, 1 eq.), phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate (220 mg, 7.3 mmol, 1 eq.) and acetonitrile (10 mL) were mixed at 25° C. under N2 overnight. Worked up by stripping off the solvents then purifying the residue over silica gel in 1:1 Hexanes/EtOAc to 100% EtOAc to 4:1 EtOAc/MeOH. Obtained 123 mg of an amorphous solid. NMR (300 MHz, CDCl3) δ 7.88 (s, 1H); 7.60 (d, 1H, J=7 Hz); 7.42 (t, 1H, J=7 Hz); 7.30 (d, 1H, J=7 Hz); 7.20-7.00 (m, 2H); 6.91 (t, 2H, J=7 hz); 4.17 (s, 3H); 3.97 (m, 1H); 3.80 (m, 1H); 2.70-2.40 (m, 6H); 2.34 (s, 3H); 1.90-1.70 (m, 2H); 1.18 (d, 3H, J=7 Hz).

Workup

  1. customthen purifying the residue over silica gel in 1:1 Hexanes/EtOAc to 100% EtOAc to 4:1 EtOAc/MeOH

Sources & evidence

ORD record
ord-8ae96b6b41ce4efca840fedacff7a776
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

Loading…