Hydrochloric Acid → N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide

HRID 41209Notes

Reaction equation

HRID 41209 reaction equation
Cl.[CH3:2][N:3]([CH3:35])[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH:16]3[CH2:20][CH2:19][CH2:18][N:17]3C(OC(C)(C)C)=O)[CH:15]=1)[O:12][C:11]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[CH:10][C:9]2=[O:34])=[O:5]>C(Cl)Cl>[CH3:2][N:3]([CH3:35])[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[CH:15]=1)[O:12][C:11]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[CH:10][C:9]2=[O:34])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86672429HCID 86672429, compound

Product 1

HCID 86672428N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamideYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (4.50 mL, 18 mmol, 4M solution) was added to a stirred solution of tert-butyl 2-(6-(dimethylcarbamoyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (850 mg, 1.80 mmol) dissolved in DCM (10 mL) at room temperature and stirred for 8 h. After evaporation of the volatile, DCM (5 mL) and MeOH (5 mL) were added followed by 10% methanolic ammonia (7 N, 5 mL) in DCM. The solid was filtered, washed with a 1:1 mixture of DCM and MeOH. The solvent was evaporated to dryness to afford after trituration with diethyl diethyl ether, N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (675 mg, 101%) as a pale beige solid. Mass Spectrum: m/z [M+H]+=372.

Workup

  1. customAfter evaporation of the volatile, DCM (5 mL) and MeOH (5 mL)
  2. additionwere added
  3. filtrationThe solid was filtered
  4. washwashed with a 1:1 mixture of DCM and MeOH
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-ea02b2e732534875be8870fae6b21dd7
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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