Ethylenediamine → HCID 178492644, compound

HRID 545192Notes

Reaction equation

HRID 545192 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([NH:33][C:34]5[N:38]=[CH:37][N:36](COCC[Si](C)(C)C)[N:35]=5)[CH:28]=4)[O:23]3)[CH2:19][CH2:18]2)=[O:16])[CH:4]=1.C(O)(C(F)(F)F)=O.C(N)CN>C(Cl)(Cl)Cl.[OH-].[Na+]>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:18][CH2:19][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([NH:33][C:34]5[NH:38][CH:37]=[N:36][N:35]=5)[CH:28]=4)[O:23]3)[CH2:21][CH2:22]2)=[O:16])[CH:4]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 67169618HCID 67169618, compound

Product 1

HCID 178492644HCID 178492644, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-6-[1-(2-trimethylsilanylethoxymethyl)-1H-[1,2,4]triazol-3-ylamino]spiro[chroman-2,4′-piperidin]-4-one (27.0 mg, 0.0419 mmol) was dissolved in CHCl3 (1 mL), and TFA (1 mL) and ethane-1,2-diamine (35.0 mg, 0.583 mmol) was added thereto. After stirring at room temperature for 16 h, the reaction mixture was diluted with CHCl3 and 1N NaOH aq. The aqueous layer was extracted with CHCl3 and combined organic layer was washed with brine, dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel thin-layer chromatography (CHCl3/MeOH=9/1) to obtain the intended compound as a yellow foam. 1H-NMR (400 MHz, CDCl3) δ7.95 (1H, d, J=2.8 Hz), 7.93 (1H, s), 7.76 (1H, dd, J=8.4, 1.2 Hz), 7.61 (1H, dd, J=8.8, 2.8 Hz), 7.46 (1H, dd, J=8.4, 8.4 Hz), 7.19 (1H, br s), 7.11 (1H, s), 7.08 (1H, d, J=8.4, 1.2 Hz), 6.93 (1H, d, J=8.8 Hz), 4.50-4.60 (1H, m), 4.08 (3H, s), 4.03 (3H, s), 3.90-4.10 (1H, m), 3.50-3.65 (1H, m), 3.25-3.40 (1H, m), 2.73 (1H, d, J=16.8 Hz), 2.68 (1H, d, J=16.8 Hz), 2.15-2.30 (1H, m), 1.95-2.10 (1H, m), 1.50-1.90 (2H, m). MS [M+H]+=515.

Workup

  1. extractionwas extracted with CHCl3 and combined organic layer
  2. washwas washed with brine
  3. dry with materialdried over MgSO4
  4. customThe desiccant was removed through filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel thin-layer chromatography (CHCl3/MeOH=9/1)

Sources & evidence

ORD record
ord-9bd0514889b545b9aa8e2faee7937267
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

Loading…