1,1'-Carbonyldiimidazole → HCID 86597129, compound

HRID 1987386Notes

Reaction equation

HRID 1987386 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][CH2:23][CH2:24][NH2:25])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:26]([N:33]1C=CN=C1)(N1C=CN=C1)=[O:27].CCN(C(C)C)C(C)C.N[OH:48].O>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][CH2:23][CH2:24][N:25]([OH:48])[C:26]([NH2:33])=[O:27])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 22235265Hydroxylamine monohydrateHCID 67423294HCID 67423294, compound

Product 1

HCID 86597129HCID 86597129, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridine-1′-yl)-butylamine (105 mg, 0.31 mmol) in THF (5 mL) was added 1,1′-carbonyldiimidazole (80 mg, 0.49 mmol) and after 40 min, the mixture was concentrated in vacuo. The residue was re-dissolved in DMF (5 mL) and treated with DIPEA (0.43 mL, 2.45 mmol) and NH2OH.H2O salt (136 mg, 1.96 mmol) and the reaction mixture was stirred overnight. Then the mixture was diluted with CH2Cl2 (25 mL) and washed with brine (5×15 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford a pale yellow oil. Purification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 25:1:1→10:1:1) afforded the product as a white foam (54 mg, 44%). 1H NMR (CDCl3) δ 0.78 (br s, 4H), 1.53-1.68 (m, 3H), 1.92-2.07 (m, 3H), 2.14 (br s, 2H), 2.44 (s, 6H), 2.72 (br s, 3H), 3.96 (d, 2H), J=9.0 Hz), 5.64 (s, 1H), 7.08 (dd, 2H, J=6.0, 3.0 Hz), 7.44 (d, 2H, J=6.0 Hz), 8.46 (s, 3H), 10.35 (s, 1H). 13C NMR (CDCl3) δ 19.23, 23.18, 25.48,27.98, 31.87, 39.16, 51.27, 53.81, 64.16, 71.47, 122.42, 131.42, 139.24, 147.06, 160.33, 162.15. ES-MS m/z 398 [M+H]+. Anal. Calcd. for C22H31N5O2.0.3CH2Cl2: C, 63.32; H, 7.53; N, 16.56. Found: C, 63.13; H, 7.68; N, 16.46.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in DMF (5 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 pale yellow oil
  8. customPurification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 25:1:1→10:1:1)

Sources & evidence

ORD record
ord-6b8d95b51f5048e79ddc86288028589a
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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