1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86721270, compound

HRID 1750428Notes

Reaction equation

HRID 1750428 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([OH:21])=O)[N:17]=2)=[CH:4][CH:3]=1.CCN=C=N[CH2:27][CH2:28][CH2:29][N:30](C)C.C1C=CC2N(O)N=NC=2C=1.[O:43]1[CH2:48]CC(CCN)[CH2:45][CH2:44]1>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([NH:30][CH2:29][CH:28]3[CH2:27][CH2:48][O:43][CH2:44][CH2:45]3)=[O:21])[N:17]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 86721269HCID 86721269, compound

Product 1

HCID 86721270HCID 86721270, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (122 mg, 0.402 mmol) obtained in step 8, WSC (116 mg, 0.603 mmol), HOBt (92.0 mg, 0.603 mmol), TEA (0.112 mL, 0.804 mmol) and 2-(tetrahydro-2H-pyran-4-yl)ethanamine (56.0 mg, 0.483 mmol) in DMF (1.6 mL) was stirred at 100° C. for 1 hr. The reaction mixture was cooled, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (3×10 mL). 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; 0→10% methanol/ethyl acetate) to give 2-{2-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}-N-(tetrahydro-2H-pyran-4-ylmethyl)acetamide (117 mg, 73%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  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; 0→10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-5415a14de65a43b28b19e4094081fa17
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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