Hydrochloric Acid → HCID 178478692, compound

HRID 1916836Notes

Reaction equation

HRID 1916836 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14]CC(=O)NCCCCCCCC)[N:10]=[C:9]1[NH2:27])=O)(C)(C)C.[N:28]#CN.C(O)C.[ClH:34]>O.CO>[ClH:34].[ClH:34].[NH2:28][CH2:14][CH2:13][C:11]1[N:10]=[C:9]([NH2:27])[NH:8][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9864CyanamideHCID 67061961HCID 67061961, compound

Product 1

HCID 178478692HCID 178478692, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,4-diamino-2-butanone dihydrochloride 25 (0.300 g, 1.71 mmol) and cyanamide (0.753 g, 17.9 mmol) were dissolved in water (10 mL). The pH of the solution was adjusted to pH=4.3 before heating the reaction at 95° C. for 3.5 h while open to the atmosphere. After cooling to ambient temperature ethanol (10 mL) was added to the flask and the solution was evaporated to dryness. Purification of the residue by column chromatography (MeOH sat. with NH3/CH2Cl2 90:10) yielded the product as its corresponding free base: Addition of methanol (10 mL) and concentrated hydrochloric acid followed by evaporation in vacuo afforded the target compound 26 (0.211 g, 62%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 6.21 (s, 1H), 5.14 (br s, 2H), 2.81 (m, 2H), 2.47 (m, 2H); HRMS (ESI) calcd for C5H11N4 (MH+) 127.0978. Found 127.0977.

Workup

  1. temperaturebefore heating
  2. customthe reaction at 95° C. for 3.5 h while open to the atmosphere
  3. additionwas added to the flask
  4. customthe solution was evaporated to dryness
  5. customPurification of the residue by column chromatography (MeOH sat. with NH3/CH2Cl2 90:10)
  6. customyielded the product as its corresponding free base
  7. customfollowed by evaporation in vacuo

Sources & evidence

ORD record
ord-5d2f3eeb703f40659d33e23e171c1e00
Source dataset
uspto-grants-2013_12
Patent number
US08618149B2

Reaction notes

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