Triethylamine → HCID 58997125, compound

HRID 251067Notes

Reaction equation

HRID 251067 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:16][C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.CCN(CC)CC.ClC(OC1C=C[C:40]([N+:43]([O-:45])=O)=CC=1)=O.N[OH:47].Cl>C(Cl)Cl.O>[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:16][C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:40]([NH:43][OH:45])=[O:47])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 67272305HCID 67272305, compound

Product 1

HCID 58997125HCID 58997125, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-[(3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-amino]-butan-1-ol (0.230 g, 0.673 mmol) and Et3N (0.136 g, 1.35 mmol) in dry CH2Cl2 (8 mL) was added 4-nitrophenyl chloroformate (0.163 g, 0.808 mmol). After the mixture was stirred overnight, water (20 mL) was added and the mixture was extracted with CH2Cl2 (3×20 mL). The extracts were combined, and dried over anhydrous Na2SO4 to afford a yellow oil. The oil was dissolved in CH2Cl2 (5 mL), and NH2OH.HCl (0.046 g, 0.66 mmol) and Et3N (0.101 g, 1.00 mmol) were added. The mixture was stirred for 24 h, and water (20 mL) was added. The mixture was extracted CH2Cl2 (3×20 mL). The extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (6:1 EtOAc/MeOH), affording a pale yellow solid (0.113 g, 42%) after precipitation from CH2Cl2/hexanes by evaporation under vacuum. 1H NMR (CDCl3) δ 0.99 (d, 6H, J=6.9 Hz), 1.46-1.61 (m, 4H), 2.17 (s, 3H), 2.27 (s, 3H), 2.52-2.57 (m, 2H), 2.96 (septet, 1H, J=6.9 Hz), 3.72 (s, 2H), 3.73 (s, 2H), 4.03 (t, 2H, J=5.7 Hz), 7.15 (dd, 1H, J=4.8, 7.8 Hz), 7.26 (s, 1H), 7.53 (dd, 1H, J=1.2, 7.8 Hz), 7.76 (s, br. 1H), 8.18 (s, 1H), 8.32 (dd, 1H, J=1.2, 4.8 Hz); 13C NMR (CDCl3) δ 18.03, 22.48, 2.28, 26.88, 27.29, 54.03, 57.91, 58.58, 65.39, 123.10, 132.21, 133.21, 133.96, 139.18, 144.26, 145.51, 146.01, 153.81, 155.54, 159.25. ES-MS m/z 423 (M+Na). Anal. Calcd. for C22H32N4O3.0.3CH2Cl2.0.2C6H14: C, 63.68; H, 8.05; N, 12.64. Found: C, 63.58; H, 8.10; N, 12.82.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. customto afford a yellow oil
  4. stirringThe mixture was stirred for 24 h
  5. extractionThe mixture was extracted CH2Cl2 (3×20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationAfter filtration the solvent
  8. customwas removed by evaporation under vacuum
  9. customthe residue was purified by flash chromatography on a silica gel column (6:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-61766bab4a1440cf86e1eb3eb215e043
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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