Hydrochloric Acid → HCID 18705855, compound

HRID 2287840Notes

Reaction equation

HRID 2287840 reaction equation
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:10]([C:14](OC)=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C([NH2:31])=O.C[O-].[Na+].CO.Cl>CN(C=O)C>[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:10]([C:14]([NH2:31])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 887MethanolHCID 10942334Sodium MethoxideHCID 18705832HCID 18705832, compound

Product 1

HCID 18705855HCID 18705855, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-(dipropylamino)-2,3-dihydro-6-(phenylmethoxy)-1H-indene-5-carboxylate (74, 0.95 g, 2.5 mmol) and formamide (1.1 g, 25 mmol) in DMF (10 mL) at 100° C. was added 25% sodium methoxide in methanol (2.5 mmol, 0.57 mL) dropwise. The mixture stirred for 2 h. The reaction was cooled to rt and quenched with water (100 mL). The resulting precipitate was stirred for 0.5 h and the solvent was removed via filtration. This solid was crystallized from EtOAc/MeOH to give a white solid that was converted into the HCl salt and crystallized from EtOAc/MeOH to give the title compound 78 as a white solid (m.p. 247-248° C.).

Workup

  1. customquenched with water (100 mL)
  2. stirringThe resulting precipitate was stirred for 0.5 h
  3. customthe solvent was removed via filtration
  4. customThis solid was crystallized from EtOAc/MeOH
  5. customto give a white solid
  6. customcrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-6f76abb42c664ce3989aa476aea77c6d
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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