Aniline → HCID 16666414, compound

HRID 219643Notes

Reaction equation

HRID 219643 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=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]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=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 249036332-(Pyridin-2-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 16666414HCID 16666414, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (100 mg, 0.5 mmol, prepared according to the general procedure described in Example 2, steps 1 and 2), 1-hydroxybenzotriazole (76.1 mg, 0.56 mmol) and PS-DCC (518 mg, 1.28 mmol/g, 0.66 mmol) in 8 mL of DMF is shaken at room temperature for 15 minutes, and aniline (31 mg, 0.33 mmol) is added. After shaking at room temperature for 18 hours, PS-trisamine (400 mg, 3.75 mmol/g, 1.5 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 to yield 2-pyridin-2-yl-pyrimidine-5-carboxylic acid phenylamide (21 mg, 23%) as a solid. MS: 277 (M+H).

Workup

  1. customprepared
  2. stirringAfter shaking at room temperature for 18 hours
  3. stirringthe mixture is continually shaken at room temperature for 18 hours
  4. filtrationThe solid is filtered
  5. washwashed with DCM
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-0213044da0f147e29213fde0d4b2177d
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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