Hydrazine hydrate (1:1) → HCID 67959966, compound

HRID 1529429Notes

Reaction equation

HRID 1529429 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]([O:22]C)=O)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].O.[NH2:25][NH2:26]>CCO>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]([NH:25][NH2:26])=[O:22])[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67958038HCID 67958038, compound

Product 1

HCID 67959966HCID 67959966, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 5-(6-isopropoxypyrazin-2-yl)-1H-indole-3-carboxylate (10 g, 30 mmol) in EtOH (50 mL) was added hydrazine hydrate (30 mL) and the reaction was heated at reflux for 48 h. The reaction was cooled to RT and a white precipitate was formed. The suspension was filtered and dried to afford 5-(6-isopropoxypyrazin-2-yl)-1H-indole-3-carbohydrazide (9.0 g, 90.9%) as a white solid. MS (ESI, pos. ion) m/z: 312 (M+1); 1H-NMR (DMSO-d6) δ ppm; 11.71 (s, 1H), 9.2 (s, 1H), 8.8 (d, J=1.6 Hz, 1H), 8.71 (s, 1H), 8.1 (s, 1H), 8.0 (s, 1H), 7.90 (dd, J=8.4, 1.6 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 5.4 (m, 1H), 4.35 (d, J=2 Hz, 1H), 1.4 (d, J=6.0 Hz, 6H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 48 h
  3. customa white precipitate was formed
  4. filtrationThe suspension was filtered
  5. customdried

Sources & evidence

ORD record
ord-63b4783d43014d7cb88116e915eea547
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…