1,1'-Carbonyldiimidazole → HCID 86597130, compound

HRID 1987387Notes

Reaction equation

HRID 1987387 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][CH2:22][NH2:23])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:24]([N:31]1C=CN=C1)(N1C=CN=C1)=[O:25].CCN(C(C)C)C(C)C.N[OH:46].Cl>C1COCC1.C(Cl)Cl>[CH3:20][C:19]1[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]2[CH2:21][CH2:22][N:23]([OH:46])[C:24]([NH2:31])=[O:25])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67422263HCID 67422263, compound

Product 1

HCID 86597130HCID 86597130, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-yl)-ethylamine (84 mg, 0.27 mmol) in THF (3 mL) was added 1,1′-carbonyldiimidazole (44 mg, 0.27 mmol) and the mixture was heated to 60° C. After 2 h, the mixture was concentrated in vacuo. The residue was re-dissolved in DMF (3 mL) and treated with DIPEA (0.13 mL, 1.35 mmol) and NH2OH.HCl (75 mg, 1.08 mmol) and the reaction mixture was stirred overnight. Then the mixture was diluted with CH2Cl2 (20 mL) and washed with brine (5×15 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford a yellow oil. Purification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 25:1:1) afforded the product as a white solid (27 mg, 27%). 1H NMR (CDCl3) δ 1.53-1.57 (m, 1H), 1.70 (d, 2H, J=15.0 Hz), 1.92-2.09 (m, 5H), 2.43-2.45 (m, 8H), 3.86 (d, 2H, J=9.0 Hz), 4.70 (br s, 1H), 6.43 (br s, 1H), 7.09 (dd, 2H, J=6.0, 3.0 Hz), 7.46 (d, 2H, J=9.0 Hz), 8.53 (d, 2H, J=3.0 Hz), 10.07 (br s, 1H). 13C NMR (CDl3) δ 19.33, 24.96, 33.13, 38.80, 55.54, 66.00, 122.70, 130.80, 139.36, 147.73, 161.02, 162.06. ES-MS m/z 370 [M+H]+. Anal. Calcd. for C20H27N5O2.0.2CH2Cl2: C, 62.78; H, 7.15; N, 18.12. Found: C, 62.86; H, 7.46; N, 17.97.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in DMF (3 mL)
  3. washwashed with brine (5×15 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a yellow oil
  8. customPurification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 25:1:1)

Sources & evidence

ORD record
ord-3c8f971a04be4f3daf57d2f078268941
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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