Dimethylformamide → HCID 59634109, compound

HRID 1615074Notes

Reaction equation

HRID 1615074 reaction equation
Cl.[CH2:2]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([OH:20])[CH2:19][NH:18][CH2:17]3)=[CH:12][C:11]=2[O:21][CH3:22])=[CH:6][CH:5]=1)[CH3:3].CCN=C=NCCCN(C)C.Cl.[CH:37]1[CH:38]=[CH:39][C:40]2[N:45](O)N=N[C:41]=2[CH:42]=1.CN(C=[O:51])C>O.C(N(CC)CC)C>[CH2:2]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([OH:20])[CH2:19][N:18]([C:41]([C:40]4[CH:39]=[CH:38][CH:37]=[CH:42][N:45]=4)=[O:51])[CH2:17]3)=[CH:12][C:11]=2[O:21][CH3:22])=[CH:6][CH:5]=1)[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66792457HCID 66792457, compound2×

Product 1

HCID 59634109HCID 59634109, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]-azetidin-3-ol hydrochloride (0.50 g) prepared in (3), 2-pyridinecalboxylic acid (0.070 g), WSC.HCl (0.12 g) and HOBt.H2O (0.092 g) in DMF (3.0 mL) was added triethylamine (0.070 mL). The reaction mixture was stirred at RT for 15 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. A mixed solvent of chloroform/hexane was added the residue. The precipitated solid was collected on a filter and dried to give the title compound (0.15 g, 74%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. additionA mixed solvent of chloroform/hexane was added the residue
  5. customThe precipitated solid was collected on
  6. filtrationa filter
  7. customdried

Sources & evidence

ORD record
ord-9521a2d503ae419cb77eb6f312dcf530
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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