Hydrochloric Acid → 6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one

HRID 41204Notes

Reaction equation

HRID 41204 reaction equation
Cl.[N:2]1([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([CH:20]4[CH2:24][CH2:23][CH2:22][N:21]4C(OC(C)(C)C)=O)[CH:19]=2)[O:16][C:15]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:14][C:13]3=[O:38])=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1>C(Cl)Cl>[N:2]1([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([CH:20]4[CH2:24][CH2:23][CH2:22][NH:21]4)[CH:19]=2)[O:16][C:15]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[CH:14][C:13]3=[O:38])=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86672425tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate

Product 1

HCID 866724156-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-oneYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl 4M (9.74 mL, 39 mmol) was added to a stirred solution of tert-butyl 2-(6-(morpholine-4-carbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (2 g, 3.89 mmol) dissolved in DCM (15 mL) at r.t and stirred over the week-end. After concentration, DCM (15 mL) and MeOH (15 mL) were added, followed by a solution of 10% methanolic ammonia (7 N) in DCM (10 mL). The crude product was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 0 to 10% methanol in DCM. The solvent was evaporated to dryness to give a solid and dried under vacuum to give 6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one (1.0 g, 62%) as a beige solid. Mass Spectrum: m/z [M+H]+=414.

Workup

  1. concentrationAfter concentration, DCM (15 mL) and MeOH (15 mL)
  2. additionwere added
  3. custompurified by flash chromatography on silica gel eluting with 0 to 10% methanol in DCM
  4. customThe solvent was evaporated to dryness
  5. customto give a solid
  6. customdried under vacuum

Sources & evidence

ORD record
ord-190175ec38204e3e950aba4aa02ef4e8
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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