Dimethylformamide → HCID 18433061, compound

HRID 2305544Notes

Reaction equation

HRID 2305544 reaction equation
[NH2:1][CH2:2][CH:3]([OH:24])[CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:7]=1.CN([CH:28]=[O:29])C>>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:8]2[CH:7]=[C:6]([NH:5][CH2:4][CH:3]3[O:24][C:28](=[O:29])[NH:1][CH2:2]3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 6228Dimethylformamide2×HCID 9797296HCID 9797296, compound

Product 1

HCID 18433061HCID 18433061, compoundYield 73%

Conditions

Temperature
60 °C

Procedure

To a 0° C. solution of (RS)-1-amino-3-[2-(4-methoxy-phenyl)-quinolin-4-ylamino]-propan-2-ol (0.139 g) 0.429 mmol) in DMF (2.5 ml) was added dropwise a solution of 1,1-carbonyldiimidazole (0.076 g, 0.472 mmol) in DMF (1 ml). After 20 min. at 0° C., and 1.5 hours at 60° C., the reaction mixture was cooled to room temperature and concentrated. Addition of H2O provided (RS)-5-{[2-(4-methoxy-phenyl)-quinolin-4-ylamino]-methyl}-oxazolidin-2-one (0.110 g, 73%) as yellowish solid, MS: m/e=349 (M+).

Workup

  1. concentrationconcentrated
  2. additionAddition of H2O

Sources & evidence

ORD record
ord-eb3cc04066374d87aae82339ea94b637
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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