1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86721232, compound

HRID 1750390Notes

Reaction equation

HRID 1750390 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[C:17]([CH2:19][C:20]([OH:22])=O)[N:18]=2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:44]1[CH2:49][CH2:48][CH:47]([CH2:50][NH2:51])[CH2:46][CH2:45]1>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[C:17]([CH2:19][C:20]([NH:51][CH2:50][CH:47]3[CH2:48][CH2:49][O:44][CH2:45][CH2:46]3)=[O:22])[N:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27732104-AminomethyltetrahydropyranHCID 86721230HCID 86721230, compound

Product 1

HCID 86721232HCID 86721232, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (225 mg, 0.709 mmol) obtained in step 5, WSC (204 mg, 1.06 mmol), HOBt (163 mg, 1.06 mmol), TEA (0.198 mL, 1.42 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (98.0 mg, 0.851 mmol) in DMF (2.8 mL) was stirred at 100° C. for 1 hr. The reaction solution was cooled, added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 1→10% methanol/ethyl acetate) to give the title compound (192 mg, 65%) as a yellow powder.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 1→10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a2b7e89afb7647fba40d9116fdd4b15f
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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