1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90029569, compound

HRID 1488018Notes

Reaction equation

HRID 1488018 reaction equation
[CH:1]([C:4]1[NH:5][C:6]([CH3:20])=[C:7]([C:9]2[C:10]([CH3:19])=[CH:11][C:12]([CH3:18])=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[N:8]=1)([CH3:3])[CH3:2].Cl.[NH:22]1[CH2:25][CH:24]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[CH2:23]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH:1]([C:4]1[NH:5][C:6]([CH3:20])=[C:7]([C:9]2[C:10]([CH3:19])=[CH:11][C:12]([CH3:18])=[C:13]([CH:17]=2)[C:14]([N:22]2[CH2:25][CH:24]([C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=3)[CH2:23]2)=[O:16])[N:8]=1)([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 552549914-(Azetidin-3-yl)benzonitrile hydrochloride2×HCID 90029728HCID 90029728, compound2×

Product 1

HCID 90029569HCID 90029569, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The mixture of 5-(2-isopropyl-5-methyl-1H-imidazol-4-yl)-2,4-dimethylbenzoic acid (compound 159.3, 250 mg, 0.92 mmol), 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2, 195 mg, 1.0 mmol), EDCI (264 mg, 1.4 mmol), HOBt (170 mg, 1.0 mmol) and DIEA (640 μL, 3.7 mmol) in DMF (10 mL) was stirred at room temperature for 16 hours. The reaction was diluted with saturated NaHCO3 and extracted with EtOAc (60 mL). The organic phase was washed with brine (3×20 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative TLC with 8% methanol in dichloromethane and lyophilized to give 85 mg (22%) of the title compound as a white solid. m/z (ES+) 413 (M+H)+.

Workup

  1. extractionextracted with EtOAc (60 mL)
  2. washThe organic phase was washed with brine (3×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC with 8% methanol in dichloromethane

Sources & evidence

ORD record
ord-fa0b000e594843bba9ab8606caa5c586
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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