Pyridine → HCID 145857630, compound

HRID 2216116Notes

Reaction equation

HRID 2216116 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].[CH2:54]([NH2:57])[CH2:55][NH2:56].C(N(CC)CC)C>C(Cl)Cl>[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[NH:31][C:42]([NH:56][CH2:55][CH2:54][NH2:57])=[O:43])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 1049PyridineHCID 3301EthylenediamineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857630HCID 145857630, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 25: step c) 0.150 g, 0.290 mmol) in dry CH2Cl2 (10 mL) was treated with pyridine (0.026 mL, 0.319 mol) and p-nitrophenyl chloroformate (0.064 g, 0.319 mmol) and stirred 1.7 h. The reaction mixture was treated with ethylene diamine (0.194 mL, 2.90 mmol) and triethylamine (0.485 mL, 3.48 mmol) and stirred at room temperature 16 h. The reaction was diluted with CH2Cl2 and washed with water (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the product [(4-{2′-[3-(2-amino-ethyl)-ureido]-6′-methyl-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester (0.145 g, 82%) as a tan solid. 1H NMR (MeOD): δ 8.195 (s, 1H), 8.057 (d, 1H, J=8.0 Hz), 7.902 (t, 1H, J=1.6 Hz), 7.718 (t, 1H, J=8.0 Hz), 7.554 (d, 1H, J=8.0 Hz), 7.511 (d, 1H, J=8.0 Hz), 7.289 (t, 1H, J=7.6 Hz), 7.119 (d, 1H, J=7.2 Hz), 3.099 (m, 2H), 2.676 (s, 3H), 2.621 (m, 2H), 2.007 (s, 3H), 1.511 (s, 9H). C27H33N5O5S3: 604.16 (M+1) found 603.90.

Workup

  1. stirringstirred at room temperature 16 h
  2. washwashed with water (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97c46cf6247f496a8088acc302ba7738
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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