1,1'-Carbonyldiimidazole → HCID 59464208, compound

HRID 1713737Notes

Reaction equation

HRID 1713737 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[C:18]([NH:20][NH2:21])=[O:19])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([NH:32][C:33](=S)OC2C(F)=C(F)C(F)=C(F)C=2F)[CH:29]=[CH:30][CH:31]=1)[CH3:24].C1N=CN(C(N2C=NC=C2)=O)C=1>CN(C=O)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C:18]3[O:19][C:33]([NH:32][C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH2:23][CH3:24])[CH:27]=4)=[N:21][N:20]=3)=[O:22])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 57830811HCID 57830811, compound2×HCID 59464200HCID 59464200, compound2×

Product 1

HCID 59464208HCID 59464208, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-[4-(4-Acetylpiperazin-1-yl)phenyl]-2-hydrazino-2-oxoacetamide (Intermediate 21, 153 mg, 0.5 mmol) was added to a solution of O-(pentafluorophenyl) (3-ethoxyphenyl)thiocarbamate (Intermediate 48, 182 mg 0.5 mmol) in DMF (7 mL). The mixture was stirred at 60° C. for 30 min then PS-CDI (500 mg 1.0 mmol) was added and stirring was continued for a further 2 hours. The mixture was allowed to cool then filtered to remove the resin, which was washed with a further 2×10 mL DMF. The combined filtrates were concentrated by evaporation to give a solid that was then triturated with 1:1 acetonitrile:water to give the title compound (220 mg) as a solid; 1H NMR δ 10.95 (1H, s), 10.85 (1H, s), 7.67 (2H, d), 7.33-7.22 (2H, m), 7.12 (1H, d), 6.97 (2H, d), 6.64 (1H, d), 4.04 (2H, q), 3.65-3.51 (4H, m), 3.11 (4H, d), 2.07 (3H, s), 1.35 (3H, t); MS m/e MH+ 451.

Workup

  1. stirringstirring
  2. waitwas continued for a further 2 hours
  3. temperatureto cool
  4. filtrationthen filtered
  5. customto remove the resin, which
  6. washwas washed with a further 2×10 mL DMF
  7. concentrationThe combined filtrates were concentrated by evaporation
  8. customto give a solid
  9. customthat was then triturated with 1:1 acetonitrile

Sources & evidence

ORD record
ord-5e280339f10b4acbb19ae2f74b2a2b74
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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