Methylhydrazine → HCID 13754299, compound

HRID 1249504Notes

Reaction equation

HRID 1249504 reaction equation
[CH3:1][NH:2][NH2:3].[C:4]([NH:6][C:7](=[N:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][N:19]=[C:20]2[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)SC)#[N:5]>CN(C=O)C>[NH2:5][C:4]1[N:6]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][N:19]=[C:20]3[N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[N:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 13754294HCID 13754294, compound

Product 1

HCID 13754299HCID 13754299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Methyl hydrazine (5.7 ml) is added to a stirred suspension of 1-cyano-3-[3-(1-piperidino-5-isoquinolyloxy)propyl]-2-methylpseudothiourea (7.77 g) in 62 ml of DMF under nitrogen. The reaction mixture is stirred at 40° C. under nitrogen for 24 hours, cooled to RT, evaporated under vacuo and the residue dissolved in warm absolute ethanol. The resulting precipitate is collected, washed with absolute ethanol and dried in air. The filtrate is evaporated in vacuo and the residue crystallized from acetonitrile and dried overnight, yielding 5.3 g of the crude product as an off-white solid, M.P. 173°-175°0 C. The crude product is placed on a silica gel column and eluted with methylene chloride/methanol. The combined pure fractions are evaporated and recrystallized from acetonitrile, yielding the desired product, M.P. 181°-182° C.

Workup

  1. temperaturecooled to RT
  2. customevaporated under vacuo
  3. dissolutionthe residue dissolved in warm absolute ethanol
  4. customThe resulting precipitate is collected
  5. washwashed with absolute ethanol
  6. customdried in air
  7. customThe filtrate is evaporated in vacuo
  8. customthe residue crystallized from acetonitrile
  9. customdried overnight
  10. customyielding 5.3 g of the crude product as an off-white solid, M.P. 173°-175°0 C
  11. washeluted with methylene chloride/methanol
  12. customThe combined pure fractions are evaporated
  13. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ebdf8b51306441f9813b7ca95ff6e5c1
Source dataset
uspto-grants-1986_12
Patent number
US04632927

Reaction notes

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