1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178472468, compound

HRID 1713755Notes

Reaction equation

HRID 1713755 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N:10]=[C:11]=S.[NH:13]([C:15](=[O:37])[C:16]([NH:18][C:19]1[CH:36]=[CH:35][C:22]([O:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:21][CH:20]=1)=[O:17])[NH2:14].CCN=C=NCCCN(C)C>CC(N(C)C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH:10][C:11]1[O:37][C:15]([C:16]([NH:18][C:19]2[CH:36]=[CH:35][C:22]([O:23][C@H:24]3[CH2:25][CH2:26][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:29]3)=[CH:21][CH:20]=2)=[O:17])=[N:13][N:14]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 27607942,4,5-TrifluorophenylisothiocyanateHCID 178472470HCID 178472470, compound2×

Product 1

HCID 178472468HCID 178472468, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2,4,5-trifluorophenyl isothiocyanate (70 mg, 0.37 mmol) in DMA (1 mL) was added in one portion to a stirred solution of ethyl trans-4-(4-{[hydrazino(oxo)acetyl]amino}-phenoxy)cyclohexanecarboxylate (Intermediate 80, 129 mg, 0.37 mmol) in DMA (3 mL) and the reaction mixture was stirred at room temperature for 1 h. EDCI (71 mg, 0.37 mmol) was added in one portion and the reaction mixture was heated to 85° C. for 20 minutes in a microwave. The mixture was cooled to room temperature and a further portion of EDCI (7.1 mg, 0.04 mmol) was added and the reaction mixture stirred at 85° C. for 10 minutes in a microwave. The reaction mixture was concentrated in vacuo to leave a solid, which was recrystallised (CH3CN) to give the title compound (125 mg, 69%) as a solid; 1H NMR δ1.33 (3H, t), 1.48-1.58 (2H, m), 1.68-1.72 (2H, m), 2.06-2.10 (2H, m), 2.18-2.22 (2H, m), 2.45-2.53 (1H, m), 4.21 (2H, q), 4.39-4.46 (1H, m), 7.07-7.11 (2H, d), 7.81-7.84 (2H, d), 7.80-7.91 (1H, m), 8.29-8.36 (1H, m), 11.12-11.25 (1H, m); MS m/e MH+ 505.

Workup

  1. temperaturethe reaction mixture was heated to 85° C. for 20 minutes in a microwave
  2. temperatureThe mixture was cooled to room temperature
  3. stirringthe reaction mixture stirred at 85° C. for 10 minutes in a microwave
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customto leave a solid, which
  6. customwas recrystallised (CH3CN)

Sources & evidence

ORD record
ord-76580047cbef461ba1fe45510be1bb28
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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