Dicyclohexylcarbodiimide → HCID 178438883, compound

HRID 872453Notes

Reaction equation

HRID 872453 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:10]([OH:12])=O)[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[O:40][C:39]([CH2:41][CH:42]([NH2:44])[CH3:43])=[CH:38][CH:37]=2)[CH:32]=[CH:33][C:34]=1[Cl:35]>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([NH:44][CH:42]([CH3:43])[CH2:41][C:39]2[O:40][C:36]([C:31]3[CH:32]=[CH:33][C:34]([Cl:35])=[C:29]([Cl:28])[CH:30]=3)=[CH:37][CH:38]=2)=[O:12])[NH:8][N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 630839371-(5-(3,4-Dichlorophenyl)furan-2-yl)propan-2-amineHCID 178441096HCID 178441096, compound

Product 1

HCID 178438883HCID 178438883, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

5-Tert-butyl-2H-pyrazole-3-carboxylic acid (94 mg; 0.55 mmol) was dissolved in DCM:DMF (4:1, 5 ml). DCC (172 mg; 0.83 mmol) was added. 1-(5-(3,4-dichlorophenyl)furan-2-yl)propan-2-amine (149 mg; 0.55 mmol) was dissolved in 2 ml of DCM and TEA (77 μl, 0.55 mmol) and the resulting solution was added to the reaction mixture. The reaction mixture was stirred overnight at RT. Then DCM (50 ml) was added and organic phase was washed with water (2×30 ml). The organic phase was dried over Na2SO4, evaporated and purified by chromatography (CombiFlash, 1st column silica, eluent: 7.5-100% EtOAc/heptane; 2nd column silica, eluent: 0-5% MeOH/DCM) to give 35 mg (15%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.19 (d, 3H), 1.27 (s, 9H), 2.88 (dd, 1H), 2.98 (dd, 1H), 4.33 (quintet, 1H), 6.29 (d, 1H), 6.33 (s, 1H), 7.00 (d, 1H), 7.60 (m, 2H), 7.83 (d, 1H), 7.89 (d, 1H), 12.84 (s, 1H).

Workup

  1. washorganic phase was washed with water (2×30 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by chromatography (CombiFlash, 1st column silica, eluent: 7.5-100% EtOAc/heptane; 2nd column silica, eluent: 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-f55c70dfff4043209fa6cfa65874be83
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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