Tetrahydrofuran → HCID 86758813, compound

HRID 1635926Notes

Reaction equation

HRID 1635926 reaction equation
[N+:1](C1C=CC=CC=1CC(O)=O)([O-:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27]1[C:31]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[C:30]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[NH:29][N:28]=1.[CH2:45]1CCN2[C:48](=NCCC2)[CH2:47][CH2:46]1.[O:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1>>[F:44][C:41]1[CH:42]=[CH:43][C:38]([C:30]2[NH:29][N:28]=[C:27]([NH:26][C:60](=[O:56])[CH:59]([C:58]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:57]=3)[N+:1]([O-:3])=[O:2])[C:31]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[CH:39][CH:40]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 77337(2-Nitrophenyl)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 155131015-(4-Fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-amine

Product 1

HCID 86758813HCID 86758813, compoundYield 14%

Procedure

Under a stream of argon gas, 543 mg of 2-nitrophenylacetic acid and 486 mg of carbonyldiimidazole were dissolved in 10 ml of tetrahydrofuran, followed by stirring at room temperature for 10 minutes. Then, 254 mg of 3-amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole and 457 mg of DBU were added thereto, followed by stirring at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the resulting residue was suspended in chloroform, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was purified by column chromatography using 40 g of silica gel [with an elution solvent comprising chloroform-methanol (100:1)]. Thus, 70 mg (14% yield) of the title compound was obtained as a white powder.

Workup

  1. stirringby stirring at room temperature overnight
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-cc06a8f82a774264a211d7527115512d
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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