1,1'-Carbonyldiimidazole → HCID 10298358, compound

HRID 968762

Reaction equation

HRID 968762 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:25]1([CH2:28][NH:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH:35]([O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=3)[CH2:34][CH2:33]2)[CH2:27][CH2:26]1>C1COCC1>[CH:25]1([CH2:28][N:29]([CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][CH:35]([O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=3)[CH2:36][CH2:37]2)[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5984364-Fluoro-3-methoxybenzoic acidHCID 70015962HCID 70015962, compound

Product 1

HCID 10298358HCID 10298358, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-fluoro-3-methoxybenzoic acid (0.082 g) in THF (1 ml) was added carbonyldiimidazole (0.078 g) and the resulting solution stirred at room temperature for 10 minutes before addition of the product of Step e (0.15 g) in THF (1.5 ml). The mixture was stirred for 2 hours and the solvent removed by evaporation to yield a colourless gum. Purification by reverse phase HPLC (with a gradient eluent system 25% MeCN/NH4OAc(aq) (0.1%) to 95% MeCN//NH4OAc(aq) (0.1%)) gave the title compound (0.011 g).

Workup

  1. customthe solvent removed by evaporation
  2. customto yield a colourless gum
  3. customPurification by reverse phase HPLC (with a gradient eluent system 25% MeCN/NH4OAc(aq) (0.1%) to 95% MeCN//NH4OAc(aq) (0.1%))

Sources & evidence

ORD record
ord-28bc4efa037d41d68eda45ca1d52b28e
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Linked notes

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