Tris(hydroxymethyl)aminomethane → HCID 16043211, compound

HRID 219637Notes

Reaction equation

HRID 219637 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.N=C=N.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[CH2:29]([NH:36][C:13]([C:10]1[CH:11]=[N:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1)=[O:15])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 7473892-Phenylpyrimidine-5-carboxylic acid

Product 1

HCID 16043211HCID 16043211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenyl-pyrimidine-5-carboxylic acid, (80 mg), 1-hydroxybenzotriazole (92 mg) and polymer supported-carbodiimide (640 mg, 1.25 mmol/g) in 8 mL of DCM is shaken at room temperature for 30 min and benzylamine (43 mg) is added. After shaking at room temperature for 1.5 days, PS-trisamine (295 mg, 4.08 mmol/g) is added. The mixture is continually shaken at room temperature for 16 hours. The solid is filtered and washed with DCM. The filtrate is concentrated to yield of 2-phenyl-pyrimidine-5-carboxylic acid benzylamide (98 mg, 85%) as a solid. MS: 290 (M+H); 1H NMR (CDCl3): 9.17 (s, 2H), 8.50 (d, 2H), 7.52-7.55 (m, 3H), 7.36-7.40 (m, 5H), 6.54 (broad, H), 4.69-4.71 (d, 2H); IC50=10 nM.

Workup

  1. stirringAfter shaking at room temperature for 1.5 days
  2. stirringThe mixture is continually shaken at room temperature for 16 hours
  3. filtrationThe solid is filtered
  4. washwashed with DCM
  5. concentrationThe filtrate is concentrated to yield of 2-phenyl-pyrimidine-5-carboxylic acid benzylamide (98 mg, 85%) as a solid

Sources & evidence

ORD record
ord-826ab34908654358a488819feec3f245
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…