Hydrazinecarboxylic acid, ethyl ester → HCID 136596965, compound

HRID 1476834Notes

Reaction equation

HRID 1476834 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([N:13]2[CH2:17][CH2:16][CH:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[NH:26]([C:28](OCC)=[O:29])[NH2:27]>CN1C(=O)CCC1.CO>[NH2:18][CH:15]1[CH2:16][CH2:17][N:13]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]3[NH:2][C:28](=[O:29])[NH:26][N:27]=3)[N:4]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90393161HCID 90393161, compound

Product 1

HCID 136596965HCID 136596965, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
175 °C

Procedure

To a crude reaction mixture containing tert-butyl (1-(3-cyanoisoquinolin-1-yl)pyrrolidin-3-yl)carbamate (786 mg) was added ethyl hydrazinecarboxylate (242 mg, 2.323 mmol) in NMP (5 mL). The resulting suspension was heated at 175° C. overnight and was subsequently cooled, diluted with MeOH, and filtered. The crude product was purified using mass-triggered HPLC eluting with a gradient of 20-45% ACN in water (acid mode). The product-containing fractions were concentrated to give the title compound (117 mg, 17.0% over 2 steps). ESI-MS m/z [M+H]+ 297.5.

Workup

  1. customTo a crude reaction mixture
  2. temperaturewas subsequently cooled
  3. filtrationfiltered
  4. customThe crude product was purified
  5. washeluting with a gradient of 20-45% ACN in water (acid mode)
  6. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-a515fc3e5c3d4953bdbbeebaba529984
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…