1,1'-Thiocarbonyldiimidazole → HCID 178527156, compound

HRID 851884Notes

Reaction equation

HRID 851884 reaction equation
[O:1]=[S:2]1(=[O:26])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([C:19](=[N:21][OH:22])[NH2:20])[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:23][CH2:24][CH2:25][C:4]2=[N:3]1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[S:28].C1CCN2C(=NCCC2)CC1>CC#N>[O:26]=[S:2]1(=[O:1])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([C:19]4[NH:20][C:27](=[S:28])[O:22][N:21]=4)[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:23][CH2:24][CH2:25][C:4]2=[N:3]1

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86595484HCID 86595484, compound

Product 1

HCID 178527156HCID 178527156, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of the product obtained in Step A of Example 13 (300 mg, 0.81 mmol) in 6 ml of CH3CN there are added 239 mg (1.21 mmol) of thiocarbonyldiimidazole and then 481 μl (3.22 mmol) of DBU. The reaction solution is stirred at ambient temperature for 1 hour. Evaporation to dryness and chromatography on silica (CH2Cl2/MeOH 95/5) are carried out. After evaporating the fractions containing the product formed, the residue is triturated in MeOH and the title product is recovered by filtration.

Workup

  1. customEvaporation to dryness and chromatography on silica (CH2Cl2/MeOH 95/5)
  2. customAfter evaporating the fractions
  3. additioncontaining the product
  4. customformed
  5. customthe residue is triturated in MeOH
  6. filtrationthe title product is recovered by filtration

Sources & evidence

ORD record
ord-2a3e3516fb8a4010bc314e1929fcebe7
Source dataset
uspto-grants-2007_08
Patent number
US07253163B2

Reaction notes

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