Pyridine → HCID 145857654, compound

HRID 723143Notes

Reaction equation

HRID 723143 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[NH2:31])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:42](OC1C=CC([N+]([O-])=O)=CC=1)=[O:43].[C:54]([N:73]1[N:77]=[N:76][C:75]([CH2:78][CH2:79][CH2:80][CH2:81][NH2:82])=[N:74]1)([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8](=[NH:9])[C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[NH:31][C:42]([NH:82][CH2:81][CH2:80][CH2:79][CH2:78][C:75]3[N:76]=[N:77][N:73]([C:54]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[N:74]=3)=[O:43])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 21886092HCID 21886092, compoundHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857654HCID 145857654, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {[4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (60 mg, 0.116 mmol), as prepared according to the procedure of step c of Example 25, and pyridine (10 mg, 0.128 mmol) in DCM (1.1 mL) was added 4-nitrophenyl chloroformate (23 mg, 0.116 mmol), and stirred at ambient temperature for 4 h. To the above mixture was added a solution of 4-(2-trityl-2H-tetrazol-5-yl)-butylamine (65 mg, 0.151 mmol) in DCM (0.65 mL), and stirred for 48 h. The mixture was concentrated and purified on a preparative TLC plate (1000 μm), developing with EtOAc/DCM (5 and 20%) to give the title compound (15 mg, 14% yield) as a yellow solid.

Workup

  1. stirringstirred for 48 h
  2. concentrationThe mixture was concentrated
  3. custompurified on a preparative TLC plate (1000 μm)

Sources & evidence

ORD record
ord-811ff5de960f40e4b49255cf9c63972e
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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