Ethanolamine → HCID 86749355, compound

HRID 1440810Notes

Reaction equation

HRID 1440810 reaction equation
[OH:1][C@H:2]1[C@H:11]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]3[C:23](=[O:31])[C:24](=[O:30])[C:25]=3OC(C)C)[CH:9]=2)[O:4][C:3]1([CH3:33])[CH3:32].[CH2:34]([CH2:36][NH2:37])[OH:35]>CC#N.O>[OH:1][C@H:2]1[C@H:11]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]3[C:23](=[O:31])[C:24](=[O:30])[C:25]=3[NH:37][CH2:36][CH2:34][OH:35])[CH:9]=2)[O:4][C:3]1([CH3:32])[CH3:33]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 86749353HCID 86749353, compound

Product 1

HCID 86749355HCID 86749355, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 529 mg(1.18 mmol) of 3-[trans-3-hydroxy-2,2-dimethyl-4-(1-oxo-1,3-dihydroisoindol-2-yl)-chroman-6-yl]-4-isopropoxy-cyclobut-3-ene- 1,2-dione as prepared in Example 3 in CH3CN (20 mL) and ethanolamine (716 μL; 11.8 mmol) was stirred at room temperature for 4 days. The reaction mixture was heated at 50° C. for 1 h, cooled to room temperature, diluted with H2O, and extracted into 20% THF/CH2Cl2. The organic extracts were dried over MgSO4 and purified by flash chromatography (CH2Cl2 : MeOH :NH4OH (93.25; 4.5; 2.25)) followed by trituration from MeOH/ether to give 124 mg of the title compound as a tan solid, mp 205°-215° C.: 1H-NMR (DMSO-d6 ; 400 MHz) δ8.93 (t, 1 H), 7.79 (dd, 1 H), 7.74 (s, 1 H), 7.69 (dd, 1 H), 7.5-7.64 (m, 3 H), 7.00 (d, 1 H), 5.75 (d, 1 H), 5.2-5.5 (br, 1 H), 4.86 (t, 1 H), 4.4-4.5 (br d, 1 H), 3.67 (m, 2 H), 3.53 (q, 3 H), and 1.27 ppm (s, 3 H); IR (KBr) 1780, 1710, 1660, and 1600 cm-1 ; mass spectrum (+FAB), m/e 449 (M +H), and 471 (M+Na). Anal. Calcd. for C25H24N2O6. 1 H2O C, 64.37; H, 5.62; N, 6.01 Found: C, 64.32; H, 5.83; N, 6.18.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted into 20% THF/CH2Cl2
  3. dry with materialThe organic extracts were dried over MgSO4
  4. custompurified by flash chromatography (CH2Cl2 : MeOH :NH4OH (93.25; 4.5; 2.25))

Sources & evidence

ORD record
ord-01b341a0d7944d90a935bc7ff9cbb3fe
Source dataset
uspto-grants-1996_03
Patent number
US05500442

Reaction notes

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