Diisopropylethylamine → HCID 118451757, compound

HRID 1054223Notes

Reaction equation

HRID 1054223 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23](OCC)=[O:24])[C:13]1=[O:28].[NH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].CCN(C(C)C)C(C)C>O1CCOCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([NH:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:24])[C:13]1=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 118451779HCID 118451779, compound

Product 1

HCID 118451757HCID 118451757, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension of ethyl 1-(benzo[d]thiazol-2-ylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate (930 mg, 2.346 mmol), tert-butyl 2-aminoacetate (369 mg, 2.82 mmol) in dioxane (5 mL) was added DIPEA (410 μl, 2.346 mmol). Reaction mixture was heated at 100° C. for 12 h. Solvent from reaction mixture was distilled out to get crude product which was then column purified using 15% EtOAC in hexane to get titled product in 43% yield.

Workup

  1. customReaction mixture
  2. customSolvent from reaction mixture
  3. distillationwas distilled out
  4. customto get crude product which
  5. customcolumn purified

Sources & evidence

ORD record
ord-126073f906b84940989312386ecd033b
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

Loading…