Diisopropylethylamine → 6-Chloro-8-[(2,6-difluorobenzyl)oxy]-N-[(2R)-1,5-dihydroxypentan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide

HRID 1624129Notes

Reaction equation

HRID 1624129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:5]2[N:6]([C:8]([C:12](O)=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:7]=1.[NH2:25][C@H:26]([CH2:29][CH2:30][CH2:31][OH:32])[CH2:27][OH:28].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:5]2[N:6]([C:8]([C:12]([NH:25][C@H:26]([CH2:29][CH2:30][CH2:31][OH:32])[CH2:27][OH:28])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867178796-Chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 86718199(R)-2-Amino-1,5-pentanediol

Product 1

HCID 867181986-Chloro-8-[(2,6-difluorobenzyl)oxy]-N-[(2R)-1,5-dihydroxypentan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under argon, 70 mg (0.20 mmol) of 6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]-pyridine-3-carboxylic acid were dissolved in 0.63 ml of dry dimethylformamide, 33.1 mg (0.28 mmol, 1.4 equivalents) of (2R)-2-aminopentan-1,5-diol, 98 μl of diisopropylethylamine (0.60 mmol, 3 equivalents) and 98 mg of HATU (0.26 mmol, 1.3 equivalents) were added and the mixture was stirred at room temperature overnight. A little water was then added, and the mixture was purified directly by preparative HPLC (Method 10). This gave 31.4 mg of the target compound (35% of theory).

Workup

  1. customthe mixture was purified directly by preparative HPLC (Method 10)

Sources & evidence

ORD record
ord-f6555c3e71814f2c9d63a43dc1b08913
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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