Hydrazine hydrate (1:1) → HCID 136500864, compound

HRID 1056288Notes

Reaction equation

HRID 1056288 reaction equation
[C:1]([C:4]1[NH:5][C:6]([C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[N:15]=[C:16]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]([CH3:23])=[N:18]3)=[CH:7][C:8]=1[C:9]([O:11]C)=O)(=O)[CH3:2].O.[NH2:30][NH2:31]>C(O)C>[C:25]([NH:24][C:16]1[C:17]([CH3:23])=[N:18][C:19]2[C:14]([N:15]=1)=[C:13]([C:6]1[NH:5][C:4]3[C:1]([CH3:2])=[N:30][NH:31][C:9](=[O:11])[C:8]=3[CH:7]=1)[CH:22]=[CH:21][CH:20]=2)([CH3:27])([CH3:28])[CH3:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89783513HCID 89783513, compound

Product 1

HCID 136500864HCID 136500864, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of methyl 2-acetyl-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (416b) (0.141 g, 0.37 mmol), hydrazine monohydrate (Fluka, 0.020 mL, 0.408 mmol) in Ethanol (1.23 mL) was heated to 75° C. for 24 h. Reaction mixture was directly loaded on silica gel samplet and purified by Biotage (30-100% EtOAc:EtOH (3:1)/hexanes) to produce 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-7-methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (416) (33 mg, 0.091 mmol, 24% yield) that solidified as yellow solid upon drying. 1H NMR (300 MHz, MeOH) δ ppm 1.67 (s, 9H) 2.56-2.70 (m, 1H) 7.30-7.40 (m, 1H) 7.40-7.50 (m, 1H) 7.40-7.55 (m, 1H) 7.76-7.87 (m, 1H) 8.03-8.16 (m, 1H). m/z (ESI, +ve) 363.0 (M+H).

Workup

  1. customReaction mixture
  2. custompurified by Biotage (30-100% EtOAc:EtOH (3:1)/hexanes)

Sources & evidence

ORD record
ord-fafd2478ca1641c89b1c03af82e39dfe
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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