Aniline → HCID 59805830, compound

HRID 219687Notes

Reaction equation

HRID 219687 reaction equation
[CH:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.NC1C=CC=CC=1.C(O)C(N)(CO)CO>CN(C=O)C>[C:21]1([NH:17][C:13]([C:10]2[CH:11]=[N:12][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[N:8][CH:9]=2)=[O:15])[CH:22]=[CH:23][CH:24]=[CH:25][CH:20]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 62757161HCID 62757161, compound

Product 1

HCID 59805830HCID 59805830, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-cyclohexyl-pyrimidine-5-carboxylic acid (100 mg, 0.48 mmol), 1-hydroxybenzotriazole (74.2 mg, 0.55 mmol), and PS-DCC (505 mg, 1.28 mmol/g, 0.65 mmol) in DMF (8 mL) is shaken at room temperature for 15 minutes, and aniline (30 mg, 0.32 mmol) is added. The mixture is shaken at room temperature for 18 hours, PS-trisamine (388 mg, 3.75 mmol/g, 1.45 mmol) is added and the mixture is continually shaken at room temperature for 18 hours. The solid is filtered and washed with DCM. The filtrate is concentrated in vacuo to afford 2-cyclohexyl-pyrimidine-5-carboxylic acid phenylamide (45.6 mg, 51%) as a solid. MS: 282 (M+H); IC50=4960 nM.

Workup

  1. stirringThe mixture is shaken at room temperature for 18 hours
  2. stirringthe mixture is continually shaken at room temperature for 18 hours
  3. filtrationThe solid is filtered
  4. washwashed with DCM
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-541d2f4292934cada2eae82d7d6fdddf
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…