1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500664, compound

HRID 1713751Notes

Reaction equation

HRID 1713751 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=S.[NH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=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:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[NH:13][C:1]1[O:43][C:22]([C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C@H:32]3[CH2:33][CH2:34][C@H:35]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH2:36][CH2:37]3)=[CH:30][CH:31]=2)=[O:24])=[N:20][N:21]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78747AminopyrazineHCID 11412697Thiocarbonyl diimidazoleHCID 178500682HCID 178500682, compound2×

Product 1

HCID 178500664HCID 178500664, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Thiocarbonyl diimidazole (179 mg, 1.00 mmol) was added in one portion to a solution of aminopyrazine (96 mg, 1.00 mmol) in DMA (5 mL) and the solution was stirred at room temperature for 6 h. Methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]-acetate (Intermediate 43, 267 mg, 0.80 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 20 h and then heated at 80° C. for 10 minutes in the microwave. The solution was cooled to room temperature and EDCI (192 mg, 1.00 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 15 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 as an off white solid (35 mg, 8%); 1H NMR δ 1.15 (2H, m), 1.45-1.48 (2H, m), 1.79 (6H, m), 2.26 (2H, d), 2.45-2.49 (1H, m), 3.61 (3H, s), 7.23-7.25 (2H, d), 7.69-7.71 (2H, d), 8.36 (1H, d), 8.42 (1H, t), 9.19 (1H, s), 11.01 (1H, s); MS m/e MH+ 437.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 20 h
  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 15 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-24db6fa8264a4729a29df407c651134d
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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