Pyridine → 5-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentylphosphonic acid

HRID 2216084Notes

Reaction equation

HRID 2216084 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].Cl[C:36](OC1C=CC([N+]([O-])=O)=CC=1)=[O:37].N1C=CC=CC=1.C([O:56][P:57]([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][NH2:67])(=[O:61])[O:58]CC)C.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([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:36](=[O:37])[NH:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][P:57](=[O:61])([OH:56])[OH:58])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[O:34])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 19977767HCID 19977767, compoundHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 1458576785-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentylphosphonic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{[4-(6′-Amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.100 g, 0.204 mmol), (Example 25: step c), 4-nitrophenyl chloroformate (0.041 g, 0.204 mmol), pyridine (0.018 g, 0.224 mmol), DCM [3 mL] were added to a flask containing a stirbar. This solution was stirred at room temperature for 2.5 hours. To this solution was added (5-Amino-pentyl)-phosphonic acid diethyl ester (0.136 g, 0.611 mmol) and Triethylamine (0.062 g, 0.611 mmol). Solution was stirred at room temperature for 18 hours. Reaction was concentrated in vacuo followed by chromatography (50%–100% EtOAc/Hx) to yield title compound (0.138 g, 88%). ESI-MS (m/z): Calcd. for C34H47N4O8PS3: 767.93 (M+H); found 667.1.

Workup

  1. additioncontaining a stirbar
  2. stirringSolution was stirred at room temperature for 18 hours
  3. customReaction
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9b11f3190e49442a82fcde5e3e08bcda
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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