Hydrochloric Acid → HCID 90020562, compound

HRID 2200091Notes

Reaction equation

HRID 2200091 reaction equation
Cl.C(=[N:15][C:16]1[CH:17]=[C:18]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[O:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([CH:29]2[CH2:31][CH2:30]2)=[O:28])[CH:21]=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[NH2:15][C:16]1[CH:17]=[C:18]([CH:32]=[C:33]([CH3:35])[CH:34]=1)[O:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([CH:29]2[CH2:31][CH2:30]2)=[O:28])[CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118223425HCID 118223425, compound

Product 1

HCID 90020562HCID 90020562, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1M HCl aqueous solution (10 mL) to a solution of the imine obtained in Step 3 (450 mg, 1.0 mmol) in THF (10 mL), stir the reaction at room temperature for 1 hr. Basicify with saturated NaHCO3 solution, extract with EtOAc (30 mL×2). Combine the organic layers, dry over anhydrous Na2SO4. Concentration and purification by chromatography (silica gel, EtOAc:PE=1:1) afford the title compound (230 mg, 80.8%). MS: (M+1): 285.2.

Workup

  1. customthe reaction at room temperature for 1 hr
  2. extractionBasicify with saturated NaHCO3 solution, extract with EtOAc (30 mL×2)
  3. dry with materialCombine the organic layers, dry over anhydrous Na2SO4
  4. concentrationConcentration and purification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-5c81c8432c2147919d2b3d3f6046a45a
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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