Cycloheptanecarboxylic acid → 4-(2-Cycloheptanecarbonylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole

HRID 2379891Notes

Reaction equation

HRID 2379891 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[N:11]=[C:12]([N:15]=[C:16]([NH2:18])[NH2:17])[S:13][CH:14]=2)[N:9]=1.[CH:19]1([C:26](O)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[CH:19]1([C:26]([NH:3][CH2:4][C:5]2[S:6][CH:7]=[C:8]([C:10]3[N:11]=[C:12]([N:15]=[C:16]([NH2:18])[NH2:17])[S:13][CH:14]=3)[N:9]=2)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 15091Cycloheptanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189538344-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

Product 1

HCID 189562864-(2-Cycloheptanecarbonylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazoleYield 31.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (2.0 g), cycloheptanecarboxylic acid (1.02 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.50 g), 1-hydroxybenzotriazole hydrate (1.07 g) and triethylamine (1.24 g) in N,N-dimethylformamide (50 ml) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. The residue was suspended in water (200 ml). The mixture was alkalized to pH 11 with a saturated aqueous potassium carbonate solution and then extracted with a mixture of ethyl acetate (250 ml) and tetrahydrofuran (50 ml). The extract was dried over magnesium sulfate and then was evaporated. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol =10:1. Recrystallization from a mixture of methanol, tetrahydrofuran and diisopropyl ether afforded 4-(2-cycloheptanecarbonylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole (0.72 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with a mixture of ethyl acetate (250 ml) and tetrahydrofuran (50 ml)
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customwas evaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with a mixture of chloroform and methanol =10:1
  7. customRecrystallization
  8. additionfrom a mixture of methanol, tetrahydrofuran and diisopropyl ether

Sources & evidence

ORD record
ord-12bac91918f14f0ebefa53bde53c8b59
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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