4-Aminopyridine → HCID 178500662, compound

HRID 1713750Notes

Reaction equation

HRID 1713750 reaction equation
[C:1]([C:8]1[NH:9][CH:10]=CN=1)([C:3]1[NH:4][CH:5]=[CH:6]N=1)=S.NC1C=CN=CC=1.[NH:20]([C:22](=[O:43])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]2[CH2:37][CH2:36][C@H:35]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1)=[O:24])[NH2:21].CCN=C=NCCCN(C)C>CC(N(C)C)=O.O>[N:4]1[CH:3]=[CH:1][C:8]([NH:9][C:10]2[O:43][C:22]([C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C@H:32]4[CH2:37][CH2:36][C@H:35]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH2:34][CH2:33]4)=[CH:28][CH:27]=3)=[O:24])=[N:20][N:21]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11412697Thiocarbonyl diimidazoleHCID 178500682HCID 178500682, compound2×

Product 1

HCID 178500662HCID 178500662, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Thiocarbonyl diimidazole (190 mg, 1.06 mmol) was added in one portion to a solution of 4-aminopyridine (100 mg, 1.06 mmol) in DMA (8 mL) and the solution was stirred at room temperature for 3 h. Methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]-acetate (Intermediate 43, 284 mg, 0.85 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 30 minutes and then heated at 80° C. for 10 minutes in the microwave. The solution was cooled to room temperature and EDCI (205 mg, 1.06 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 20 minutes in the microwave. The reaction mixture was cooled to room temperature and poured into water (200 mL). The mixture was filtered and the resulting solid was recrystallised (CH3CN) to give the title compound (93 mg, 20%) as a solid; 1H NMR δ 1.15 (2H, t), 1.42-1.51 (2H, m), 1.74-1.82 (5H, m), 2.24-2.26 (2H, d), 3.61 (3H, s), 7.23 (2H, d), 7.54-7.55 (2H, m), 7.69-7.71 (2H, m), 8.43 (2H, s) MS m/e MH+ 436.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. temperatureheated at 80° C. for 10 minutes in the microwave
  3. temperatureThe solution was cooled to room temperature
  4. temperaturethe reaction mixture was heated to 90° C. for 20 minutes in the microwave
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationThe mixture was filtered
  7. customthe resulting solid was recrystallised (CH3CN)

Sources & evidence

ORD record
ord-017499a6535640c386ac1962b749ad49
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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