8-Quinolinesulfonyl chloride → HCID 59314278, compound

HRID 1047691Notes

Reaction equation

HRID 1047691 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11](Cl)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][C:18]([C:20]1([NH2:29])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:15]([O:17][C:18]([C:20]1([NH:29][S:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)(=[O:13])=[O:12])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 292208-Quinolinesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 59314278HCID 59314278, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of quinoline-8-sulfonyl chloride (400 mg, 1.76 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (361 mg, 1.76 mmol) in anhydrous DCM (8 mL) is added DIPEA (291 μL, 1.76 mmol). The resulting solution is stirred at RT overnight. The reaction solution is diluted with DCM (40 mL), washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (35) as white solid (245 mg, 35%).

Workup

  1. washwashed with water (1×5 mL) and brine (2×5 mL)
  2. dry with materialThe organic layer is dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-750bb92529a5416d9cf4f1cee0c19cff
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…