3-Pyridinemethanamine → HCID 178512714, compound

HRID 1980746Notes

Reaction equation

HRID 1980746 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.CO[C:31]1[C:35](OC)=[N:34][S:33](=[O:39])(=[O:38])[N:32]=1.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][NH2:47])[CH:41]=1>CO>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:31]2[C:35]([NH:47][CH2:46][C:42]3[CH:41]=[N:40][CH:45]=[CH:44][CH:43]=3)=[N:34][S:33](=[O:39])(=[O:38])[N:32]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178512714HCID 178512714, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 7.0 g; 23 mmoles) in 180 ml of methanol was added dropwise to a partial suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (4.1 g; 23 mmoles) in 400 ml of methanol at 8°. This was followed by 3-picolylamine (2.74 g; 25.3 mmoles) and the reaction mixture was stirred at 8° for 15 minutes and at ambient temperature for 20 hours. The reaction solution was evaporated and the residue flash chromatographed on 125 g of silica gel (230-400 mesh) using CH3CN(90):CH3OH(10):NH4OH(0.5) as the eluant. A second purification by preparative high pressure liquid chromatography on silica with CH2Cl2 (85):95%EtOH(15):NH4OH(0.5) as the mobile phase yielded 0.78 g of the title compound as a buff-colored foam containing 0.4 mole of ethanol, mp 128°-138° (foaming).

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue flash chromatographed on 125 g of silica gel (230-400 mesh)
  3. customA second purification by preparative high pressure liquid chromatography on silica with CH2Cl2 (85)

Sources & evidence

ORD record
ord-837e187edf11441b81b4584815d4d99d
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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