2-Morpholinoethylamine → HCID 56847970, compound

HRID 1798423Notes

Reaction equation

HRID 1798423 reaction equation
S=C1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][CH3:22])[CH:12]=2)=[O:8])[CH2:5][CH2:4]S1.NCC[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C1COCC1>[C:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:7](=[O:8])[NH:6][CH2:5][CH2:4][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 56847970HCID 56847970, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound VII (219.1 mg, 0.642 mmol) was dissolved in anhydrous THF (3.2 mL, 5 mL/mmol of 6). To the yellow solution was added 4-(2-aminoethyl)morpholine (83.5 mg, 84 μL, 0.642 mmol). The reaction solution was stirred for two hours, after which time the solution was colorless. The solvent was removed under reduced pressure. The crude material was purified by column chromatography on silica gel using CH2Cl2/MeOH (96:4, v/v) to give 161 mg (71%) of 17 as a white solid: mp=82-83° C. (uncorrected); Rf=0.16 (CH2Cl2/MeOH, 96:4, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8 Hz, 1H), 6.96 (d, 4J=1.65 Hz, 1H), 6.94 (dd, 3J=8 Hz, 4J=1.8 Hz, 1H), 5.23 (bs, 1H), 5.05 (s, 2H), 3.82 (s, 3H), 3.67 (m, 4H), 3.29 (m, 2H), 2.46 (t, 3J=5.9 Hz, 2H), 2.42 (bs, 41-1) and 2.29 (s, 3H). Exact mass (ESI) calculated for C17H25N2O6 [M+H]=353.1707. found 353.1705.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b20d2e3ee1044369236d0b0b5a21b35
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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