4-Methylmorpholine → HCID 86631521, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:20][CH3:21])([CH3:19])[C:16](O)=[O:17])[N:13]=2)=[N:6][CH:7]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:57]([NH:60][NH2:61])(=[O:59])[CH3:58]>C(Cl)Cl.CN(C=O)C>[C:57]([NH:60][NH:61][C:16](=[O:17])[C:15]([O:20][CH3:21])([CH3:19])[CH2:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[C:4]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[S:10][CH:11]=1)(=[O:59])[CH3:58]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
In a 20 mL scintillation vial, 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-2-methoxy-2-methylpropanoic acid (0.087 g, 0.187 mmol) was dissolved in CH2Cl2 (5 mL) and DMF (2 mL) and N-methylmorpholine (0.0309 mL, 0.281 mmol), followed by addition of HOBT. The mixture was cooled to 0° C. and EDCI (0.047 g, 0.244 mmol) was added. The resulting mixture was agitated for 30 minutes and acetohydrazide (0.021 g, 0.28 mmol) was added. The mixture was then agitated overnight, diluted with 50 mL of CH2Cl2 and washed with citric acid solution, sodium bicarbonate solution twice, dried and evaporated to give the title compound (0.0975 g, quantitative yield). Crude product was used in the next step.
Workup
- stirringThe mixture was then agitated overnight
- washwashed with citric acid solution, sodium bicarbonate solution twice
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-ce56809d42c34a89817fc06e2eee63a8
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354540B2
Reaction notes
Loading…