N,N-Dimethylglycine hydrochloride → HCID 53664767, compound

HRID 1491883Notes

Reaction equation

HRID 1491883 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][C:5](O)=[O:6].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.Cl.Cl.[NH2:35][CH2:36][C:37]1[N:42]=[C:41]([C:43]2[N:44]=[C:45]([N:48]=[C:49]([NH2:51])[NH2:50])[S:46][CH:47]=2)[CH:40]=[CH:39][CH:38]=1>CN(C)C=O.C(N(CC)CC)C>[NH2:50][C:49](=[N:48][C:45]1[S:46][CH:47]=[C:43]([C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:36][NH:35][C:5](=[O:6])[CH2:4][N:3]([CH3:8])[CH3:2])[N:42]=2)[N:44]=1)[NH2:51]

Participants

7

Reactant 4

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 53664767HCID 53664767, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of N,N-dimethylglycine hydrochloride (1.5 g), 1-hydroxybenzotriazole hydrate (1.5 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.1 g) in N,N-dimethylformamide (15 ml) was stirred for 1 hour at ambient temperature. The above mixture was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (3.0 g) and triethylamine (3.5 ml) in N,N-dimethylformamide (45 ml) and the mixture was stirred for 2 hours at ambient temperature. The solvent was removed by concentration and the residue was dissolved in a mixture of tetrahydrofuran, ethyl acetate and water. The mixture was adjusted to pH 13.5 with 5N-sodium hydroxide. The separated organic layer was washed with brine and evaporated in vacuo. The residue was triturated with ethyl acetate to give 2-(diaminomethyleneamino)-4-(6-dimethylaminoacetylaminomethylpyridin-2-yl)thiazole (1.96 g).

Workup

  1. stirringthe mixture was stirred for 2 hours at ambient temperature
  2. customThe solvent was removed by concentration
  3. dissolutionthe residue was dissolved in a mixture of tetrahydrofuran, ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. customevaporated in vacuo
  6. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-39dad6ce32a34ad9bfbc687b175dfd70
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

Loading…