1,1'-Carbonyldiimidazole → HCID 69202402, compound

HRID 2377288Notes

Reaction equation

HRID 2377288 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][NH2:23])=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.[C:37]([N:44]1[CH:48]=[CH:47][N:46]=[CH:45]1)(N1C=CN=C1)=[O:38].NCCN1C[CH2:56][O:55][CH2:54][CH2:53]1>C1COCC1>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][NH:23][C:37]([NH:44][CH2:48][CH2:47][N:46]2[CH2:45][CH2:56][O:55][CH2:54][CH2:53]2)=[O:38])=[CH:17][CH:16]=4)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4082852-MorpholinoethylamineHCID 69202811HCID 69202811, compound

Product 1

HCID 69202402HCID 69202402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Example 891D (800 mg, 1.62 mmol) in THF (15 mL) was added 1,1′-carbonyldiimidazole (320 mg, 1.94 mmol). The mixture was stirred at rt for 2 h, then a solution of 4-(2-aminoethyl)morpholine (253 mg, 1.94 mmol) in THF (3 mL) was added. The resulting mixture was stirred at rt for 6 h, then concentrated in vacuo. The residue was purified by flash chromatography eluting with EtOAc to give a crude oil. (326 mg).

Workup

  1. stirringThe resulting mixture was stirred at rt for 6 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography
  4. washeluting with EtOAc
  5. customto give a crude oil

Sources & evidence

ORD record
ord-d788f846158043b18e3406c3c1fe6e96
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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