1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90033553, compound

HRID 1488027Notes

Reaction equation

HRID 1488027 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[N:13]=[C:14]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[NH:15][C:16]=2[CH3:17])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[NH:24]1[CH2:27][CH:26]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[CH2:25]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[N:13]=[C:14]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[NH:15][C:16]=2[CH3:17])=[CH:7][C:3]=1[C:4]([N:24]1[CH2:27][CH:26]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[CH2:25]1)=[O:5]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 552549914-(Azetidin-3-yl)benzonitrile hydrochloride2×HCID 90029418HCID 90029418, compound2×

Product 1

HCID 90033553HCID 90033553, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 2,4-dimethyl-5-(5-methyl-2-(tetrahydrofuran-3-yl)-1H-imidazol-4-yl)benzoic acid (compound 171.2, 100 mg, 0.30 mmol), 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2, 71 mg, 0.37 mmol), EDCI (95 mg, 0.50 mmol), HOBt (20 mg, 0.10 mmol) and DIEA (207 μL, 1.20 mmol) in DMF (5 mL) was stirred at room temperature for 16 hours. The reaction was concentrated under reduced pressure, diluted with saturated NaHCO3 (10 mL) and extracted with EtOAc (30 mL). The organic phase was washed with brine (3×10 mL), dried over MgSO4 and concentrated under reduce pressure. The residue was purified by preparative TLC with 6% methanol in dichloromethane and lyophilized to give 16 mg (12%) of the title compound as a white solid. m/z (ES+) 441 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiondiluted with saturated NaHCO3 (10 mL)
  3. extractionextracted with EtOAc (30 mL)
  4. washThe organic phase was washed with brine (3×10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC with 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-fb64da106c904bd3af968a327892e16e
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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