Diisopropylethylamine → (S)-N'-hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidine

HRID 1672795Notes

Reaction equation

HRID 1672795 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:11]=3[C:10]2=[O:25])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(C(C)C)CC)(C)C.Cl.[NH2:36][OH:37]>C(O)C>[OH:37][N:36]=[C:1]([NH2:2])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:11]=3[C:10]2=[O:25])[CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67351154(S)-5-(3-Cyanophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

Product 1

HCID 86643699(S)-N'-hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-5-(3-Cyanophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (2.00 g, 5.69 mmol) obtained in Step 1 of Example 71 was suspended in ethanol (30 mL), and the mixture was refluxed for 5 hours after adding diisopropylethylamine (1.90 mL, 10.9 mmol) and hydroxylamine hydrochloride (761 mg, 10.9 mmol). After concentrating the mixture under reduced pressure, water was added to the resulting residue, and the precipitated white solid was filtered off to give (S)—N′-hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidine (2.10 g, 96%).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. concentrationAfter concentrating the mixture under reduced pressure, water
  3. additionwas added to the resulting residue
  4. filtrationthe precipitated white solid was filtered off

Sources & evidence

ORD record
ord-e0c695ca228b49c4b9873c86c05b4867
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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