3-Aminopropionitrile → HCID 145857614, compound

HRID 723145Notes

Reaction equation

HRID 723145 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]([C:10]1[S:11][C:12]([S:39][CH3:40])=[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:32]([NH:34][CH2:35][CH2:36][C:37]#[N:38])=[O:33])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NC(C1SC(SC)=C(S(C2C=C(C3C(C)=CC=CC=3N)C=CC=2)(=O)=O)C=1)=N)(C)(C)C.NCCC#N.[N:81]([Si](C)(C)C)=[N+:82]=[N-:83].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8](=[NH:9])[C:10]1[S:11][C:12]([S:39][CH3:40])=[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:32]([NH:34][CH2:35][CH2:36][C:37]3[N:81]=[N:82][NH:83][N:38]=3)=[O:33])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 16473-AminopropionitrileHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 145857612HCID 145857612, compoundHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857614HCID 145857614, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [(4-{2′-[3-(2-cyano-ethyl)-ureido]-6′-methyl-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester (31 mg, 51 μmol), as prepared from {[4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester and 3-aminopropionitrile according to the procedure of step e of Example 179, azidotrimethylsilane (40 μL, 0.30 mmol), dibutyltin oxide (3.5 mg, 10 μmol), and toluene (1.5 mL) was heated at 70° C. for 16 h and 80° C. for 4 h. The mixture was concentrated and purified by flash chromatography on silica gel, eluting with EtOAc/DCM (50, 100%) followed by MeOH/DCM (5, 10%) to give the title compound (14 mg, 42% yield) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography on silica gel
  3. washeluting with EtOAc/DCM (50, 100%)

Sources & evidence

ORD record
ord-11b7d6c54c834b6ea6042f3aa3fdd383
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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