Water → HCID 178471533, compound

HRID 1713766Notes

Reaction equation

HRID 1713766 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:38])[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]2[CH2:30][CH2:29][C@H:28]([CH:31]([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)=[O:17])[NH2:14].CCN=C=NCCCN(C)C.O>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:38][C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH:31]([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[O:17])=[N:13][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27607942,4,5-TrifluorophenylisothiocyanateHCID 178471535HCID 178471535, compound2×

Product 1

HCID 178471533HCID 178471533, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,4,5-Trifluorophenyl isothiocyanate (252 mg, 1.33 mmol) was added in one portion to a suspension of trans-ethyl 2-[4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclo-hexyl]propanoate (Intermediate 99, 400 mg, 1.11 mmol) in DMA (6 mL) and the reaction mixture was stirred at room temperature for 2 h. EDCI (319 mg, 1.66 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 10 mins in the microwave. The mixture was then cooled to room temperature and H2O (20 mL) was added. The mixture was filtered to leave a solid, which was washed with H2O (10 mL) to give the title compound (550 mg, 95%) as a solid; 1H NMR δ 1.1 (3H, d), 1.12-1.28 (2H, m), 1.2 (3H, t), 1.35-1.51 (2H, m), 1.52-1.64 (1H, m), 1.65-1.75 (1H, m), 1.77-1.9 (3H, m), 2.22-2.32 (1H, m), 2.38-2.51 (1H, m), 4.01-4.16 (2H, m), 7.2 (2H, d), 7.65-7.78 (1H, m), 7.69 (2H, d), 8.1-8.25 (1H, m), 10.95 (1H, s), 11.05 (1H, s); MS m/e MH+ 517.

Workup

  1. temperaturethe reaction mixture was heated to 90° C. for 10 mins in the microwave
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationThe mixture was filtered
  4. customto leave a solid, which
  5. washwas washed with H2O (10 mL)

Sources & evidence

ORD record
ord-2b7dbcfd03534824bffc10e4c3ae69ef
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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