Potassium Carbonate → 4-(6-Cyclobutanecarbonylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

HRID 2379887Notes

Reaction equation

HRID 2379887 reaction equation
[CH:1]1([C:5]([OH:7])=O)[CH2:4][CH2:3][CH2:2]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.Cl.Cl.[NH2:34][CH2:35][C:36]1[N:41]=[C:40]([C:42]2[N:43]=[C:44]([N:47]=[C:48]([NH2:50])[NH2:49])[S:45][CH:46]=2)[CH:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([C:5]([NH:34][CH2:35][C:36]2[N:41]=[C:40]([C:42]3[N:43]=[C:44]([N:47]=[C:48]([NH2:50])[NH2:49])[S:45][CH:46]=3)[CH:39]=[CH:38][CH:37]=2)=[O:7])[CH2:2][CH2:3][CH2:4]1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 19494Cyclobutanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 100422774-(6-Cyclobutanecarbonylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A mixture of cyclobutanecarboxylic acid (0.5 ml), 1-hydroxybenzotriazole hydrate (0.8 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.0 g) in N,N-dimethylformamide (5 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 (1.5 g) and triethylamine (1.8 ml) in N,N-dimethylformamide (15 ml) and the mixture was sitrred for 20 hours at ambient temperature. The reaction mixture was added a mixture of ethyl acetate tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was recrystallized from a mixture of N,N-dimethylformamide and ethyl acetate to give 4-(6-cyclobutanecarbonylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.86 g).

Workup

  1. waitthe mixture was sitrred for 20 hours at ambient temperature
  2. additionThe reaction mixture was added
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by concentration
  6. customthe residue was recrystallized from a mixture of N,N-dimethylformamide and ethyl acetate

Sources & evidence

ORD record
ord-07832cf9745d4e0b9032086195224dc3
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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