Phenylacetic Acid → HCID 178446148, compound

HRID 1787782Notes

Reaction equation

HRID 1787782 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8]/[C:7]/1=[N:16]\[NH2:17])[CH2:2][CH2:3][CH2:4][CH3:5].[C:18]1([CH2:24][C:25]([OH:27])=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN([CH:65]=[O:66])C>C(OCC)(=O)C>[CH3:65][O:66][C:21]1[CH:22]=[CH:23][C:18]([CH2:24][C:25]([NH:17]/[N:16]=[C:7]2\[NH:8][C:9](=[O:15])[C:10]3[NH:11][CH:12]=[N:13][C:14]=3[N:6]\2[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:27])=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 999Phenylacetic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178446164HCID 178446164, compound

Product 1

HCID 178446148HCID 178446148, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.30 g, 1.3 mmol), benzeneacetic acid, 4-methoxy-(0.23 g, 1.4 mmol), benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.62 g, 1.40 mmol) and triethylamine (0.53 mL, 3.8 mmol) in DMF (10 mL) were stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed sat. NaHCO3. The aqueous was extracted with ethyl acetate (3×). The combined organic layers were dried (MgSO4), filtered and concentrated to yield the desired product (560 mg, 98%). LCMS calculated for C19H25N6O3(M+H): 385.2; found: 385.2.

Workup

  1. washwashed sat. NaHCO3
  2. extractionThe aqueous was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4b8f3b3b8e9463da4c1ee9cefd4abea
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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