1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500370, compound

HRID 1713776Notes

Reaction equation

HRID 1713776 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]([C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)=[O:17])[NH2:14].CCN=C=NCCCN(C)C>CC(N(C)C)=O.O>[CH3:37][C:31]([C@H:28]1[CH2:27][CH2:26][C@H:25]([C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:16]([C:15]3[O:38][C:11]([NH:10][C:3]4[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=4[F:1])=[N:14][N:13]=3)=[O:17])=[CH:24][CH:23]=2)[CH2:30][CH2:29]1)([CH3:36])[C:32]([O:34][CH3:35])=[O:33]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27607942,4,5-TrifluorophenylisothiocyanateHCID 178500371HCID 178500371, compound2×

Product 1

HCID 178500370HCID 178500370, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2,4,5-trifluorophenyl isothiocyanate (183 mg, 0.96 mmol) in DMA (1 mL) was added in one portion to a suspension of methyl 2-[trans-4-(4-{[hydrazino(oxo)acetyl]amino}-phenyl)cyclohexyl]-2-methylpropanoate (Intermediate 105, 290 mg, 0.80 mmol) in DMA (3 mL) and the reaction mixture was stirred at room temperature for 1 h 30 mins. EDCI (230 mg, 1.20 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, poured into H2O (20 mL) and stirred for 5 mins. The mixture was centrifuged and the aqueous layer decanted off to leave a solid residue. The solid residue was taken up in H2O (5 mL), stirred for 5 mins and then centrifuged and the aqueous layer decanted off to leave a solid residue. H2O (5 mL) was added and the mixture was filtered to give the title compound (398 mg, 96%) as a solid; 1H NMR δ 1.1 (6H, s), 1.12-1.26 (2H, m), 1.36-1.5 (2H, m), 1.57-1.7 (3H, m), 1.78-1.89 (2H, m), 2.39-2.49 (1H, m), 3.6 (3H, s), 7.2 (2H, d), 7.65-7.78 (1H, m), 7.68 (2H, d), 8.12-8.24 (1H, m), 11.0 (1H, s), 11.1 (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. stirringstirred for 5 mins
  4. customthe aqueous layer decanted off
  5. customto leave a solid residue
  6. stirringstirred for 5 mins
  7. customthe aqueous layer decanted off
  8. customto leave a solid residue
  9. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-6432b5cc81d04f3db46f3a5fea4148a5
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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