Tetrahydrofuran → N-[3-[3-[[4-(2-hydroxyethyl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]-2,5-dimethylpyrazole-3-carboxamide

HRID 2352926Notes

Reaction equation

HRID 2352926 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].C1COCC1.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][OH:45])=[CH:39][CH:38]=1>CCOC(C)=O>[OH:45][CH2:44][CH2:43][C:40]1[CH:41]=[CH:42][C:37]([NH:36][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:17]=[CH:18][CH:19]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 669044-Aminophenethyl alcoholHCID 178426964HCID 178426964, compound

Product 1

HCID 178426941N-[3-[3-[[4-(2-hydroxyethyl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]-2,5-dimethylpyrazole-3-carboxamideYield 20%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 300 mg, 0.746 mmol) and THF (7.5 mL). To the resulting solution was added 2-(4-amino-phenyl)-ethanol (120 mg, 0.875 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and the resulting suspension was filtered. The solids collected were washed with 0° C. iPrOH (5 mL) and set aside. The filtrate was concentrated in vacuo and the residue obtained was dissolved in EtOAc (5 mL). The resulting solution was triturated with Hexanes (˜50 mL) to yield a precipitate. This precipitate was then filtered and washed with 0° C. iPrOH (5 mL). The solids collected were combined with those previously set aside to afford the title compound in 20% yield (0.078 g, 0.149 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. filtrationthe resulting suspension was filtered
  4. customThe solids collected
  5. washwere washed with 0° C. iPrOH (5 mL)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue obtained
  8. customThe resulting solution was triturated with Hexanes (˜50 mL)
  9. customto yield a precipitate
  10. filtrationThis precipitate was then filtered
  11. washwashed with 0° C. iPrOH (5 mL)
  12. customThe solids collected

Sources & evidence

ORD record
ord-4f27aaf5b6364fd29da5ecec1e9f8681
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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