Dichloromethane → tert-butyl N-[4-[3-(4-isothiocyanato-2-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216219Notes

Reaction equation

HRID 2216219 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].C(Cl)Cl.[C:20]([O:24][C:25](=[O:53])[NH:26][C:27]([C:29]1[S:30][C:31]([S:51][CH3:52])=[C:32]([S:34]([C:37]2[CH:38]=[C:39]([C:43]3[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][C:44]=3[CH3:50])[CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[CH:33]=1)=[NH:28])([CH3:23])([CH3:22])[CH3:21].NC(N)=S>>[C:20]([O:24][C:25](=[O:53])[NH:26][C:27](=[NH:28])[C:29]1[S:30][C:31]([S:51][CH3:52])=[C:32]([S:34]([C:37]2[CH:38]=[C:39]([C:43]3[CH:48]=[CH:47][C:46]([N:49]=[C:1]=[S:2])=[CH:45][C:44]=3[CH3:50])[CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[CH:33]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 2723790ThioureaHCID 145857675tert-butyl N-[4-[3-(4-amino-2-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857695tert-butyl N-[4-[3-(4-isothiocyanato-2-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Procedure

A solution of 1,1′-thiocarbonyldi-2(1H)-pyridone in DCM (0.25 M, 300 μL, 0.075 mmol) was added to {[4-(4′-amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 220: step b) 26 mg, 0.05 mmol) at rt. The orange color of the thiourea dissipated as the reagent was added, and a new higher spot appeared on TLC. The solvent was removed in vacuo and the residue was purified by preparative TLC to yield 23 mg of product. 1H-NMR (CDCl3): δ 8.01 (br s, 1H), 7.96 (d, 1H, J=7.4 Hz), 7.87 (s, 1H), 7.53 (m, 2H), 7.10 (d, 1H, J=7.9 Hz), 6.93 (br s, 1H), 6.87 (d, 1H, J=7.9 Hz), 2.51 (s, 3H), 2.17 (s, 3H), 1.50 (s, 9H).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-d35b4ec7b50144eab7d50ee63eb9c068
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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