Hydrochloric Acid → 2-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetic acid

HRID 589394Notes

Reaction equation

HRID 589394 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[N:19]=[CH:18][C:17]([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH2:30][C:31]([O:33]CC)=[O:32])=[N:22]2)=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].O.Cl>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[N:19]=[CH:18][C:17]([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH2:30][C:31]([OH:33])=[O:32])=[N:22]2)=[CH:16][CH:15]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89590301ethyl 2-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetate

Product 1

HCID 715719372-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetic acidYield 47.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetate (154 mg, 0.33 mmol) was dissolved in tetrahydrofuran (20 mL), and in an ice bath 10 mL aqueous solution dissolving lithium hydroxide monohydrate (70 mg, 1.67 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 and dried to obtain a white solid 69 mg, at a yield of 47.7%.

Workup

  1. additionwas added
  2. customIt was reacted at room temperature for 3 h
  3. customA solid precipitated
  4. filtrationwhich was filtered
  5. customdried

Sources & evidence

ORD record
ord-4b396e07f64640efbc1eb2364844f744
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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