1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16665859, compound

HRID 219673Notes

Reaction equation

HRID 219673 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[N:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[O:37]1[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]1>C(Cl)Cl>[O:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:13]([C:10]2[CH:11]=[N:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[N:8][CH:9]=2)=[O:15])[CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4192234-AminotetrahydropyranHCID 68554341HCID 68554341, compound

Product 1

HCID 16665859HCID 16665859, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyrimidine-5-carboxylic acid (50 mg, 0.24 mmol) in DCM (10 mL) is added 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide (50 mg, 0.26 mmol) and N-hydroxybenzotriazole (35 mg, 0.26 mmol) at room temperature. The mixture is stirred for 10 min, and tetrahydro-pyran-4-ylamine (27 mg, 0.26 mmol) is added. The mixture is stirred overnight, washed with 2N HCl (1×5 mL), saturated NaHCO3, (1×5 mL), water (lx 5 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by column chromatography eluting with 5% MeOH in DCM to afford 2-(5-methyl-[1,2,4]oxadiazole-3-yl)-pyrimidine-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide (33 mg) as a solid. MS: 290 (M+H); 1H NMR (300 MHz, CDCl3): δ 1.70 (m, 2H), 2.04 (m, 2H), 2.76 (s, 3H), 3.59 (m, 2H), 4.06 (m, 2H), 4.28 (m, 1H), 9.26 (s, 2H); IC50=513.5 nM.

Workup

  1. stirringThe mixture is stirred overnight
  2. washwashed with 2N HCl (1×5 mL), saturated NaHCO3, (1×5 mL), water (lx 5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography
  7. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-f18a7aad66314084a5fcbd6fc2514fd4
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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