Hydrochloric Acid → HCID 71572044, compound

HRID 589405Notes

Reaction equation

HRID 589405 reaction equation
[CH3:1][N:2]([C:15]1[CH:35]=[CH:34][C:18]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH2:29][C:30]([O:32]C)=[O:31])=[N:21]2)=[CH:17][CH:16]=1)[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].O.[OH-].[Li+].O.Cl>O1CCCC1>[CH3:1][N:2]([C:15]1[CH:35]=[CH:34][C:18]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH2:29][C:30]([OH:32])=[O:31])=[N:21]2)=[CH:17][CH:16]=1)[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89590298HCID 89590298, compound

Product 1

HCID 71572044HCID 71572044, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[1-[4-(N-methyl-2-naphthamido)benzyl]-1H-indazol-3-yl]acetate (about 1.0 mmol) was dissolved in tetrahydrofuran (30 mL), and in an ice bath, 20 mL aqueous solution dissolving lithium hydroxide monohydrate (210 mg, 5.0 mmol) was added. It was reacted at room temperature for 3 h, and the reaction was monitored to be complete by TLC. Water was added into the system, and adjusted to pH=3-4 with diluted hydrochloric acid. A solid precipitated, which was filtered, dried, and purified by preparative liquid phase to obtain a white solid 147 mg, at a total yield over two steps of 32.7%.

Workup

  1. additionwas added
  2. customIt was reacted at room temperature for 3 h
  3. customA solid precipitated
  4. filtrationwhich was filtered
  5. customdried
  6. custompurified by preparative liquid phase

Sources & evidence

ORD record
ord-93571ac8ed614bd79b2af0a2654bf103
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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