Benzeneacetic acid, 4-ethoxy- → HCID 22181352, compound

HRID 1796497Notes

Reaction equation

HRID 1796497 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CCN(C(C)C)C(C)C.[CH2:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=O)=[CH:31][CH:30]=1)[CH3:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:14]1([CH2:13][N:12]2[C:3]3=[N:4][CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[C:2]3[N:1]=[C:36]2[CH2:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH2:26][CH3:27])=[CH:30][CH:31]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 78631Benzeneacetic acid, 4-ethoxy-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22181400HCID 22181400, compound

Product 1

HCID 22181352HCID 22181352, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following general procedure 13B: Combined methyl 5-amino-6-[(cyclopropylmethyl)amino]nicotinate (950 mg, 4.3 mmol), DIPEA (1.1 ml), 4-ethoxyphenylacetic acid (850 mg, 4.72 mmol) and HATU (1.80, 4.74 mmol) in DMF (15 mL). The crude product was purified by flash chromatography on silica gel (EtOAc) to produce the desired product (530 mg, 34%).

Workup

  1. customThe crude product was purified by flash chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-28bb5956e8a54dfebfeb940122b969c1
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…