1,1'-Carbonyldiimidazole → HCID 67350115, compound

HRID 1672804Notes

Reaction equation

HRID 1672804 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([NH:22][NH2:23])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>C1COCC1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:20]4[O:21][C:28](=[O:29])[NH:23][N:22]=4)[CH:24]=[CH:25][CH:26]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67350136HCID 67350136, compound

Product 1

HCID 67350115HCID 67350115, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (1.0 g, 2.60 mmol) obtained in Step 2 of Example 56 was dissolved in THF (12 mL), and the mixture was stirred at room temperature for 2 hours after adding 1,1′-carbonyldiimidazole (464 mg, 2.86 mmol). After concentrating the mixture under reduced pressure, water was added to the resulting residue, and the pH was adjusted to 4 by addition of a 6 mol/L aqueous hydrochloric acid solution. The precipitated white solid was then filtered off to give (S)-5-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3,4-oxadiazol-2(3H)-one (1.07 g, quantitative).

Workup

  1. concentrationAfter concentrating the mixture under reduced pressure, water
  2. additionwas added to the resulting residue
  3. additionthe pH was adjusted to 4 by addition of a 6 mol/L aqueous hydrochloric acid solution
  4. filtrationThe precipitated white solid was then filtered off

Sources & evidence

ORD record
ord-37ac660ff4c04b619f170a63c76ea42e
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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