Triethylamine → HCID 178446155, compound

HRID 1664583Notes

Reaction equation

HRID 1664583 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([N:23]1[C:31]2[N:30]=[CH:29][NH:28][C:27]=2[C:26](=[O:32])[NH:25]/[C:24]/1=[N:33]\[NH2:34])[CH2:19][CH2:20][CH2:21][CH3:22].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(C=O)C.CCOC(C)=O>[O:32]=[C:26]1[NH:25]/[C:24](=[N:33]\[NH:34][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=[N:9]2)/[N:23]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:31]2[N:30]=[CH:29][NH:28][C:27]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576002864-(4-phenyl-1H-pyrazol-1-yl)butanoic acidHCID 178446164HCID 178446164, compound

Product 1

HCID 178446155HCID 178446155, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4-phenyl-1H-pyrazol-1-yl)butanoic acid (190 mg, 0.825 mmol), (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (195.0 mg, 0.825 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (401 mg, 0.908 mmol) and triethyl amine (0.23 ml, 1.65 mmol) in DMF (10 ml) was stirred at room temperature overnight. The mixture was diluted with EtOAc and washed with water and then brine. The organic phase was dried over Na2SO4, filtered and concentrated to yield the desired product (369 mg, 99.7% yield) as yellowish oil. LCMS calculated for C23H29N8O2 (M+H): 449.2. found: 449.2.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-50d49612f2b645fd860398a02fc2454e
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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