Diisopropylethylamine → N-(1-benzylpyrrolidin-3-yl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 2284699Notes

Reaction equation

HRID 2284699 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[C:7]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:6]=1)[CH2:2][CH3:3].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH2:55]([N:62]1[CH2:66][CH2:65][CH:64]([NH2:67])[CH2:63]1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CN(C)C=O.O>[CH2:55]([N:62]1[CH2:66][CH2:65][CH:64]([NH:67][C:11]([C:10]2[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][C:7]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:8][CH:9]=2)=[O:13])[CH2:63]1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27566131-Benzyl-3-aminopyrrolidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 900517164-(Propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid

Product 1

HCID 90051742N-(1-benzylpyrrolidin-3-yl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamideYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxylic acid (A3, 90 mg) in N,N-dimethylformamide (2 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (63 mg) and 1-hydroxybenzotriazole monohydrate (45 mg) were added at room temperature, and the mixture was stirred at the same temperature for 2 hours and 30 minutes. To the reaction mixture, N,N-diisopropylethylamine (153 μL) and 1-benzyl-3-aminopyrrolidine (53 mg) were added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, water was added. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure. The obtained solid matter was purified by basic silica gel column chromatography to obtain N-(1-benzylpyrrolidin-3-yl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (E9, 117 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. customdried under reduced pressure
  5. customThe obtained solid matter was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-47df18c470e0418eae37bf4b9197822b
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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