Triethylamine → (R)-N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-6-methyl-2-oxopyridine-1(2H)-carboxamide

HRID 931185Notes

Reaction equation

HRID 931185 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].[CH3:22][C:23]1[N:28]([C:29](O)=[O:30])[C:27](=[O:32])[CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C)C=O>[NH2:8][C:7]1[C:2]([NH:1][C:29]([N:28]2[C:23]([CH3:22])=[CH:24][CH:25]=[CH:26][C:27]2=[O:32])=[O:30])=[CH:3][CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:10]2)[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 916186162-Methyl-6-oxopyridine-1-carboxylic acid

Product 1

HCID 117966360(R)-N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-6-methyl-2-oxopyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a vial were added (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (100 μmol), 6-methyl-2-oxopyridine-1(2H)-carboxylic acid and N,N-dimethylformamide (1.5 mL) followed by O-(7-Azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) (200 μmol) and triethylamine (250 μmol). The vial was shaken for 16 h at room temperature. The mixture was concentrated via Speedvac. The residue was partitioned between dichloromethane and water. The organics were evaporated under vacuum to afford (R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-6-methyl-2-oxopyridine-1(2H)-carboxamide which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated via Speedvac
  2. customThe residue was partitioned between dichloromethane and water
  3. customThe organics were evaporated under vacuum

Sources & evidence

ORD record
ord-7e6055edf6824b6aa988eb1291fd7f5b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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