Dimethylformamide → HCID 59463240, compound

HRID 1712960Notes

Reaction equation

HRID 1712960 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1C(O)=O.C1C=CC(OP(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH2:45][CH:44]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[OH:52])[NH:43][N:42]=2)[CH:36]=1.C[N:54]([CH:56]=[O:57])C>ClCCCl>[OH:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[CH:44]1[N:43]([C:56]([NH:54][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[O:57])[N:42]=[C:41]([C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)[CH2:45]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 123414Diphenylphosphoryl azideHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

Product 1

HCID 59463240HCID 59463240, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
90 °C

Procedure

To a solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (29.7 mg, 0.146 mmol) in DCE (1 mL) was added a solution of TEA (14.8 mg, 0.146 mmol) in DCE (0.5 mL) at rt followed by the addition of a solution of diphenylphosphonic azide (40.2 mg, 0.146 mmol) in DCE (0.5 mL). The reaction mixture was heated at 90° C. for 2 h and then the solution was allowed to cool to rt and further to below −30° C., whereupon a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (35.0 mg, 0.146 mmol) in DMF (0.5 mL) was added. The mixture was shaken at rt for 16 h. The residue was partitioned between water (4 mL) and DCM (3 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 5-(2-hydroxyphenyl)-N-(5-methyl-3-phenylisoxazol-4-yl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (5.53 mg, 8.6%). LCMS: (AAC) ES+ 440.3.

Workup

  1. additionwas added
  2. customThe residue was partitioned between water (4 mL) and DCM (3 mL)
  3. extractionThe aqueous solution was extracted with DCM
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-95451a2ae7ec4ceebce0a520fae61695
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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