Hydrazine → HCID 58550577, compound

HRID 1890709Notes

Reaction equation

HRID 1890709 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([C:30](OC)=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.[NH2:35][NH2:36]>CO>[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([C:30]([NH:35][NH2:36])=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58550631HCID 58550631, compound

Product 1

HCID 58550577HCID 58550577, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl (2S)-2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′, 3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carboxylate from Step G (317 mg, 0.667 mmol) in MeOH (1 mL) was added hydrazine (1.0 mL, 32 mmol). The reaction was sealed and then heated to 70° C. for 18 hours. After cooling to ambient temperature, the bulk of the solvent was removed in vacuo. The residue was diluted with DCM (50 mL) and water (20 mL). The organics were then successively washed with water, half-saturated brine and brine before being dried over sodium sulfate. The organics were then filtered, concentrated in vacuo to give the title compound. MS: m/z=476 (M+1).

Workup

  1. customThe reaction was sealed
  2. temperatureAfter cooling to ambient temperature
  3. customthe bulk of the solvent was removed in vacuo
  4. additionThe residue was diluted with DCM (50 mL) and water (20 mL)
  5. washThe organics were then successively washed with water, half-saturated brine and brine
  6. dry with materialbefore being dried over sodium sulfate
  7. filtrationThe organics were then filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77543c4397c54d54b5e8af741586555e
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

Loading…