Dimethylformamide → HCID 178436440, compound

HRID 1615064Notes

Reaction equation

HRID 1615064 reaction equation
CS(O)(=O)=[O:3].[CH2:6]([C:8]1[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]3CNC3)=[CH:16][C:15]=2[O:24][CH3:25])=[CH:10][CH:9]=1)[CH3:7].CCN=C=NCCCN(C)C.Cl.[CH:40]1[CH:41]=[CH:42]C2N(O)N=[N:46][C:44]=2[CH:45]=1.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>O.O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:52][N:51]([C:53]([C:42]4[CH:41]=[C:40]([OH:3])[CH:45]=[CH:44][N:46]=4)=[O:54])[CH2:50]3)=[CH:16][C:15]=2[O:24][CH3:25])=[CH:26][CH:27]=1)[CH3:7]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86649374HCID 86649374, compound2×

Product 1

HCID 178436440HCID 178436440, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidine methanesulfonate (61.3 g) prepared in (3), 4-hydroxypyridine-2-calboxylic acid (22.8 g), WSC.HCl (36 g) and HOBt.H2O (29 g) in DMF (300 mL) was added triethylamine (23 mL). The reaction mixture was stirred at RT for 5 hr. Ethyl acetate, THF and water were added to the reaction mixture. The organic layer was washed with saturated aqueous NaHCO3 and water, and then pressure. Ethyl acetate (300 mL) was added to the residue and then the precipitated solid was collected on a filter and dried to give the title compound (51 g, 78%).

Workup

  1. washThe organic layer was washed with saturated aqueous NaHCO3 and water
  2. additionEthyl acetate (300 mL) was added to the residue
  3. customthe precipitated solid was collected on
  4. filtrationa filter
  5. customdried

Sources & evidence

ORD record
ord-1092aab8eebc479c975aea28a01aed74
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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