Water → HCID 67350136, compound

HRID 1672785Notes

Reaction equation

HRID 1672785 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:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:26]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:39][NH2:40].O>ClCCl>[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:23]=[CH:24][CH:25]=3)[C:20]([NH:39][NH2:40])=[O:22])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 682631,1'-CarbonyldiimidazoleHCID 67350552HCID 67350552, compound

Product 1

HCID 67350136HCID 67350136, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (1.36 g, 3.68 mmol) obtained in Step 1 was dissolved in dichloromethane (18 mL), and the mixture was stirred at room temperature for 1 hour after adding 1,1′-carbonyldiimidazole (657 mg, 4.05 mmol). Thereafter, hydrazine.monohydrate (0.53 mL, 11.0 mmol) was added to the mixture, and the mixture was stirred at room temperature for 1 hour. Then, water was added to the mixture, stirred, and the precipitated solid was filtered off. After concentrating the filtrate under reduced pressure, the residue was recrystallized from dichloromethane and water to give (S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (1.21 g, 86%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. stirringstirred
  3. filtrationthe precipitated solid was filtered off
  4. concentrationAfter concentrating the filtrate under reduced pressure
  5. customthe residue was recrystallized from dichloromethane and water

Sources & evidence

ORD record
ord-2b14931b49314656ad679b82bca2aef3
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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