Picolinic acid → Pyridine-2-carboxylic acid (1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-amide

HRID 2223697Notes

Reaction equation

HRID 2223697 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)=[O:11])[CH2:3]1.CCN(C(C)C)C(C)C.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](O)=[O:40].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:23][C:15]1[CH:14]=[C:13]([NH:12][C:10](=[O:11])[NH:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:39]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=3)=[O:40])[CH2:3]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 597159171-[2-(3-Amino-pyrrolidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea

Product 1

HCID 59715931Pyridine-2-carboxylic acid (1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 1-[2-(3-amino-pyrrolidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea (0.03 mmol) in DMF (0.3 mL) is added DIPEA (3 eq). The resulting solution is treated with a solution of pyridine-2-carboxylic acid (1.1 eq) in DMF (0.25 mL). A solution of TBTU (1.1 eq) in DMF (0.25 mL) is added. The reaction is stirred at 20 C for 45 min. The reaction mixture is evaporated to dryness. The residue is taken up in CH3CN/H2O/TFA (6:10:1; 1 mL) and is purified by preparative HPLC.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-445319c8c06c44e6bf7bdcbb6e3fe93e
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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