Diisopropylethylamine → 8-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-N-[(2R)-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:14]([C:18](O)=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:9]=[C:10]([C:12]#[CH:13])[CH:11]=1.N[C@H:27]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:28][OH:29].C([N:37](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>[F:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:14]([C:18]([NH:37][C@@H:32]([CH2:31][CH2:30][CH2:27][CH2:28][OH:29])[CH3:33])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:9]=[C:10]([C:12]#[CH:13])[CH:11]=1Participants
7
Reactant 4
HCID 81531Diisopropylethylamine
HCID 6994402(R)-2-Aminohexan-1-ol
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 867181738-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 2
Procedure
Under argon, 50 mg (0.15 mmol) of 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid were dissolved in 0.5 ml of dry dimethylformamide, 20.54 mg (0.18 mmol, 1.2 equivalents) of (R)-(−)-2-aminohexanol, 72 μl of diisopropylethylamine (0.44 mmol, 3 equivalents) and 72 mg of HATU (0.19 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 8). This gave 37.5 mg of the target compound (58% of theory).
Workup
- customthe mixture was purified directly by preparative HPLC (Method 8)
Sources & evidence
- ORD record
- ord-f6e3be61185a4272a44e1ae3a845c84e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946215B2
Reaction notes
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