2-(Isopropylamino)ethanol → HCID 58204314, compound

HRID 1498202Notes

Reaction equation

HRID 1498202 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[N:6]3[C:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)=[CH:9][C:8]([C:14]([OH:16])=O)=[N:7]3.[CH:19]([NH:22][CH2:23][CH2:24][OH:25])([CH3:21])[CH3:20].C(N(CC)CC)C>[Pd]>[OH:25][CH2:24][CH2:23][N:22]([CH:19]([CH3:21])[CH3:20])[C:14]([C:8]1[CH:9]=[C:10]2[N:6]([C:5]3[CH:17]=[CH:18][CH:2]=[CH:3][C:4]=3[O:13][CH2:12][CH2:11]2)[N:7]=1)=[O:16]

Participants

5

Reactant 3

HCID 79942-(Isopropylamino)ethanolHCID 8471TriethylamineHCID 86652301HCID 86652301, compound

Product 1

HCID 58204314HCID 58204314, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the procedure for 116, 8-bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid was reacted with 2-isopropylamino-ethanol. The intermediate formed (145 mg, 0.37 mmol) was dissolved in IMS (10 mL) and triethylamine (50 L, 0.37 mmol) then 10% Pd/C (20 mg) added before the reaction mixture stirred under hydrogen (1 atmosphere) for 2.75 h. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resultant residue was partitioned between DCM and water, the aqueous layer was isolated and extracted with DCM. The combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was dissolved in diethyl ether and the solution washed with water, dried (Na2SO4), filtered and then concentrated in vacuo to give 140 (79 mg, 68%). 1H NMR (DMSO-d6, 400 MHz): δ 7.83 (dd, J=8.0, 1.6 Hz, 1 H); 7.30 (td, J=7.6, 1.8 Hz, 1 H); 7.26-7.16 (m, 2 H); 6.54 (s, 1H); 4.67-4.53 (m, 1 H); 4.46 (t, J=6.0 Hz, 2 H); 4.35-4.27 (m, 1 H); 3.64-3.56 (m, 2 H); 3.55-3.46 (m, 2 H); 3.13 (t, J=6.0 Hz, 2 H); 1.22 (d, J=6.8 Hz, 6 H). LCMS: RT=9.00 min, M+H+=316

Workup

  1. customThe intermediate formed (145 mg, 0.37 mmol)
  2. filtrationThe reaction mixture was filtered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resultant residue was partitioned between DCM and water
  5. customthe aqueous layer was isolated
  6. extractionextracted with DCM
  7. dry with materialThe combined organic extracts dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe resultant residue was dissolved in diethyl ether
  11. washthe solution washed with water
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5babf4e492f7461a91f1be627571c18e
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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