phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate → HCID 44447136, compound

HRID 1592356Notes

Reaction equation

HRID 1592356 reaction equation
[NH2:1][C@H:2]([CH3:19])[C@@H:3]([OH:18])[CH2:4][N:5]([CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[CH3:20][N:21]1[C:25]([C:26]2[CH:27]=[C:28]([NH:32][C:33](=O)[O:34]C3C=CC=CC=3)[CH:29]=[CH:30][CH:31]=2)=[N:24][N:23]=[N:22]1>C(#N)C>[CH2:16]([N:5]([CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)[CH2:4][C@H:3]([OH:18])[C@H:2]([NH:1][C:33]([NH:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:25]2[N:21]([CH3:20])[N:22]=[N:23][N:24]=2)[CH:27]=1)=[O:34])[CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 58997665HCID 58997665, compound

Product 1

HCID 44447136HCID 44447136, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of Step g (50 mg, 0.19 mmol, 1 eq.), phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate (55 mg, 0.19 mmol, 1 eq.) and acetonitrile (3 mL) were mixed at 25° C. under N2 overnight. Worked up by stripping off the solvents then purifying the residue over silica gel in 100% EtOAc to 4:1 EtOAc/MeOH. Obtained 70 mg of a white glass as product. NMR (300 MHz, CDCl3) δ 7.86 (s, 1H); 7.6 (d, 1H, J=7 Hz); 7.38 (t, 1H, J=7 Hz); 7.29 (d, 1H, J=7 Hz); 7.20-7.00 (m, 2H); 6.92 (t, 2H, J=7 Hz); 4.13 (s, 3H) 4.05-3.85 (m, 1H); 3.80-3.60(m, 1H); 2.80-2.40 (m, 8H); 1.85-1.60 (m, 2H); 1.18 (d, 3H, J=7 Hz); 1.00 (t, 3H, J=7 Hz).

Workup

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

Sources & evidence

ORD record
ord-a8e37679b068426dae28dab54e27d5e0
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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