Hydrochloric Acid → HCID 178457313, compound

HRID 1614225Notes

Reaction equation

HRID 1614225 reaction equation
C([N:3](CC)CC)C.[N+]([O-])(O)=O.[CH3:12][C:13]1[CH:17]=[C:16](C)[N:15]([C:19]([NH2:21])=[NH:20])N=1.C1C=C2C(C(O)(O)[C:31](=O)[C:25]2=CC=1)=O.[ClH:35]>O>[ClH:35].[ClH:35].[NH:15]([CH2:16][CH2:17][CH2:13][CH:12]([NH2:3])[C:31]#[CH:25])[C:19]([NH2:21])=[NH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10236NinhydrinHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate

Product 1

HCID 178457313HCID 178457313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

Triethylamine (4.5 ml, 30 mmoles) is added to a solution of 1,4-diamine-5-hexyne dihydrochloride (1.85 g, 10 mmoles) in water (50 ml) at -10° C. To this solution 3,5-dimethylpyrazole-1-carboxamidine nitrate (2.3 g, 10.5 mmoles) is slowly added (in small portions) and the resulting mixture is stirred 2 h at -10° C., and for 3 days at room temperature after all starting materials have reacted (this is controlled by electrophoresis and ninhydrin colorimetric analysis). Then, the mixture is acidified (pH 5-6) with a 1 M solution of HCl and washed with dichloromethane (2×100 ml). The aqueous layer is concentrated under reduced pressure to a volume of 5 ml. This concentrated mixture is purified by ion exchange chromatography. (DOWEX 50W-X8, 100-200 mesch, H+Form) which is eluted by using a gradient of solution of HCl (0 to 4 N). The eluted fractions are checked by electrophoresis on silica gel plates and colorimetric analysis (ninhydrin and Sakaguchi reagent). The fractions containing the guanidino material are concentrated together under reduced pressure to give the title compound (1.7 g) as a colorless oil. NMR(1H) δ ppm. 1.76 (m, 4H); 2.96 (d,1H,J=1H2); 3.16 (m, 2H) 4.2 (m, 1H). M/Z: MH+ 155; MH± NH3 : 138; MH± NH2 --CNHNH2 =98.

Workup

  1. customfor 3 days at room temperature after all starting materials have reacted (
  2. washwashed with dichloromethane (2×100 ml)
  3. concentrationThe aqueous layer is concentrated under reduced pressure to a volume of 5 ml
  4. customThis concentrated mixture is purified by ion exchange chromatography
  5. wash(DOWEX 50W-X8, 100-200 mesch, H+Form) which is eluted
  6. additionThe fractions containing the guanidino material
  7. concentrationare concentrated together under reduced pressure

Sources & evidence

ORD record
ord-9b25e3e1ebbd43c7bd7a69b2e7876949
Source dataset
uspto-grants-1993_03
Patent number
US05196450

Reaction notes

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