Hydrochloric Acid → HCID 58345609, compound

HRID 2381234Notes

Reaction equation

HRID 2381234 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:19][CH3:20])=[CH:11][C:12]([I:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>C(OCC)(=O)C.CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([O:19][CH3:20])=[CH:11][C:12]([I:18])=[C:13]([C:14]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:16])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58345603HCID 58345603, compound

Product 1

HCID 58345609HCID 58345609, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-benzyloxy-2-iodo-4-methoxybenzoic acid (reference example 5-2) (1.92 g), piperidine (0.74 mL) and N,N-dimethylforamide (12 mL) was added 1-hydroxybenzotriazole (676 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.44 g) at room temperature. The mixture was stirred at room temperature for 6 hours. After addition of ethyl acetate, the mixture was poured into 2 mol/L hydrochloric acid. The organic layer was washed with water, an aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The mixture of the residue, aminopropylsilicagel and dichloromethane was stirred for 30 minutes. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (2.13 g).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialan aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe mixture of the residue
  5. stirringaminopropylsilicagel and dichloromethane was stirred for 30 minutes
  6. customInsoluble materials were removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc9d9ea82f104be2a6b9104c56bc1010
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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