Triethylamine → HCID 24993420, compound

HRID 1673230Notes

Reaction equation

HRID 1673230 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:22]3[CH:37]([NH:38][CH2:39][CH2:40][NH2:41])[CH2:36][C:35]([CH3:43])([CH3:42])[O:34][C:23]3=[N:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:16][CH:15]=1.CCN(CC)CC>C(Cl)(Cl)Cl.CCOC(C)=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[C:22]3[CH:37]([N:38]4[CH2:39][CH2:40][NH:41][C:1]4=[O:2])[CH2:36][C:35]([CH3:43])([CH3:42])[O:34][C:23]3=[N:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67019929HCID 67019929, compound

Product 1

HCID 24993420HCID 24993420, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1′-carbonyldiimidazole (18.1 mg, 0.11 mmol) in 5.0 mL of CHCl3 was added the product of Step B (0.07 mmol) and NEt3 (51.8 μL, 0.37 mmol) in 5.0 mL of CHCl3. The mixture was allowed to stir at rt for 2 h and then refluxed for 16 h. After cooling to rt, the reaction mixture was diluted with EtOAc (50 mL) and washed with brine (2×50 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+S cartridge using EtOAc as the eluant afforded the title compound: 1H NMR δ 1.48 (s, 3H), 1.58 (s, 3H), 2.00-2.09 (m, 2H), 3.18-3.50 (m, 4H), 4.70 (br. s, 1H), 5.44 (m, 1H), 7.00 (d, J=8.5, 2H), 7.18-7.27 (m, 4H), 7.50 (s, 1H).

Workup

  1. temperaturerefluxed for 16 h
  2. temperatureAfter cooling to rt
  3. washwashed with brine (2×50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57a3a07211d647a4823d735aced373be
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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