Hydrochloric Acid → HCID 178446838, compound

HRID 1487246Notes

Reaction equation

HRID 1487246 reaction equation
[ClH:1].O1[CH2:7][CH2:6]OCC1.[NH2:8][C:9]1[CH:13]=[C:12]([CH3:14])[NH:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(#N)CCCC>[ClH:1].[CH3:14][C:12]1[NH:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([NH:8][C:9](=[NH:8])[CH2:10][CH2:15][CH2:6][CH3:7])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 24754830Ethyl 3-amino-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 178446838HCID 178446838, compound

Reagents, catalysts & solvents 1

HCID 8061ValeronitrileSolvent

Conditions

Temperature
55 °C

Procedure

Hydrogen chloride in dioxane (4M, 308 mL, 1.2 mol) was added dropwise to ethyl 3-amino-5-methyl-1H-pyrrole-2-carboxylate (38.3 g, 228 mmol) (J. Med. Chem. 2008, 51, 68) in valeronitrile (383 mL). The resultant mixture was heated at 50° C. overnight. An additional portion of acid (160 mL, 0.64 mol) was added and the mixture heated at 55° C. overnight. The reaction mixture was cooled to room temperature, filtered and the filtrate evaporated. The residue was slurried in TBME (1200 mL) for 30 minutes then the solid filtered and washed with TMBE and dried. The title compound was obtained as a brown solid (58.9 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. filtrationthe solid filtered
  5. washwashed with TMBE
  6. customdried

Sources & evidence

ORD record
ord-3201b45b94424880a25e579aae4d0352
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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