phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate → 1-((2R,3S)-4-((3-(4-fluorophenyl)propyl)(2,2,2-trifluoroethyl)amino)-3-hydroxybutan-2-yl)-3-(3-(1-methyl-1H-tetrazol-5-yl)phenyl)urea

HRID 1592360Notes

Reaction equation

HRID 1592360 reaction equation
[NH2:1][C@H:2]([CH3:22])[C@@H:3]([OH:21])[CH2:4][N:5]([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:6][C:7]([F:10])([F:9])[F:8].[CH3:23][N:24]1[C:28]([C:29]2[CH:30]=[C:31]([NH:35][C:36](=O)[O:37]C3C=CC=CC=3)[CH:32]=[CH:33][CH:34]=2)=[N:27][N:26]=[N:25]1>C(#N)C>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][CH2:11][N:5]([CH2:6][C:7]([F:8])([F:9])[F:10])[CH2:4][C@H:3]([OH:21])[C@H:2]([NH:1][C:36]([NH:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:28]3[N:24]([CH3:23])[N:25]=[N:26][N:27]=3)[CH:30]=2)=[O:37])[CH3:22])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 58997676(2S,3R)-3-amino-1-[[3-(4-fluorophenyl)propyl](2,2,2-trifluoroethyl)amino]butan-2-ol

Product 1

HCID 444471411-((2R,3S)-4-((3-(4-fluorophenyl)propyl)(2,2,2-trifluoroethyl)amino)-3-hydroxybutan-2-yl)-3-(3-(1-methyl-1H-tetrazol-5-yl)phenyl)ureaYield 6.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of Step e (192 mg, 0.60 mmol, 1 eq.), phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate (176 mg, 0.60 mmol, 1 eq.) and acetonitrile (4 mL) were mixed at 25° C. under N2 overnight. Worked up by stripping off the solvents then purifying the residue over silica gel in 9:1 Hexanes/EtOAc to 100% EtOAc. Obtained 21 mg of a viscous oil. NMR (300 MHz, CDCl3) δ 8.35-8.20 (M, 1H); 7.79 (s, 1H); 7.70 (d, 1H, J=7 Hz); 7.45-7.20 (m, 2H); 7.10 (t, 2H, J=7 Hz); 6.93 (t, 2H, J=7 Hz); 6.20-5.80 (m, 1H); 4.05 (s, 3H); 3.93 (m, 1H); 3.80-3.40 (m, 2H); 3.25-3.05 (m, 2H); 2.85-2.40 (m, 4H); 1.85-1.60 (m, 2H); 1.20 (d, 3H, J=7 Hz); 1.00-0.70 (m, 1H).

Workup

  1. customthen purifying the residue over silica gel in 9:1 Hexanes/EtOAc to 100% EtOAc

Sources & evidence

ORD record
ord-978e6719a97a457f8a2a54543fb460c6
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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