Hydrochloric Acid → HCID 59813546, compound

HRID 1925326Notes

Reaction equation

HRID 1925326 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:25]4[C:20](=[CH:21][C:22]([O:26][C:27]5[CH:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=5)=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)=[O:15])[CH:11]=2)[C:6]([CH3:36])([CH3:35])[CH2:5]1)(=O)C.Cl>CCO>[CH3:35][C:6]1([CH3:36])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:25]4[C:20](=[CH:21][C:22]([O:26][C:27]5[CH:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=5)=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59813267HCID 59813267, compound

Product 1

HCID 59813546HCID 59813546, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-((6-(methoxy)-3-pyridinyl)oxy)-1-naphthalenecarboxamide (482 mg, 0.48 mmol) in EtOH (5.5 mL) was added concentrated aqueous HCl solution (3.3 mL). The reaction mixture was heated at 55-65° C. for 4 h, cooled to RT. EtOH was removed in vacuo. The aqueous layer was basified to pH=7-8 by adding 6M aqueous NaOH solution. The title compound was isolated by filtration and dried under high vacuum. MS (ESI, pos. ion) m/z: 440.1 (M+1). Mass Calc'd for C27H25N3O3: 439.51.

Workup

  1. temperaturecooled to RT
  2. customEtOH was removed in vacuo
  3. additionby adding 6M aqueous NaOH solution

Sources & evidence

ORD record
ord-af1709d9ae4f4c5a852df49cb61727ce
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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