1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69522970, compound

HRID 348451

Reaction equation

HRID 348451 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.[CH3:23][C:24]1[C:29](O)=[CH:28][CH:27]=[C:26](C)[N:25]=1.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.ClCCl>[CH3:27][C:26]1[C:1]([O:2][C:3](=[O:22])[CH2:4][O:5][C:6]2[N:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:8][N:7]=2)=[CH:28][CH:29]=[C:24]([CH3:23])[N:25]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 707322,6-Dimethyl-3-pyridinolHCID 69522849[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl ester

Product 1

HCID 69522970HCID 69522970, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl ester (prepared above, 50 mg, 0.17 mmol), 2,6-dimethyl-pyridin-3-ol (21 mg, 0.17 mmol) and DMAP (41 mg, 0.34 mmol) were slurried in dichloromethane. The solution was treated with (3-dimethylamino-propyl)-ethyl-carbodiimide (EDC) (54 mg, 0.28 mmol). After 1 h, thin layer chromatography indicated complete conversion. The reaction mixture was quenched with 10 mL 1 M HCl(aq) and 30 mL dichloromethane. The phases were partitioned, and the aqueous phase extracted with 5 mL dichloromethane. The organic phases were combined and sequentially washed with 10 mL portions of 0.1 M HCl(aq), saturated. NaHCO3(aq) and brine. The organic layer was dried using Na2SO4, filtered and concentrated. The resulting 31 mg of off-white solid was chromatographed over SiO2 (5% methanol/dichloromethane) to yield 21 mg (31%) of the titled compound. ESI-MS z/z 397 (MH+), 395 (M−H−).

Workup

  1. customThe reaction mixture was quenched with 10 mL 1 M HCl(aq) and 30 mL dichloromethane
  2. customThe phases were partitioned
  3. extractionthe aqueous phase extracted with 5 mL dichloromethane
  4. washsequentially washed with 10 mL portions of 0.1 M HCl(aq)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting 31 mg of off-white solid was chromatographed over SiO2 (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7c2bfd226611437088d8a1a060901427
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Linked notes

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