Hydrochloric Acid → 2-[1-[4-(6-fluoro-2-naphthamido)benzyl]-1H-indazol-3-yl]acetic acid

HRID 589387Notes

Reaction equation

HRID 589387 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]([CH2:29][C:30]([O:32]CC)=[O:31])=[N:21]3)=[CH:17][CH:16]=1)=[O:13])[CH:6]=[CH:5]2.O.[OH-].[Li+].O.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][N:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]([CH2:29][C:30]([OH:32])=[O:31])=[N:21]3)=[CH:17][CH:16]=1)=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89590305ethyl 2-[1-[4-(6-fluoro-2-naphthamido)benzyl]-1H-indazol-3-yl]acetate

Product 1

HCID 715718332-[1-[4-(6-fluoro-2-naphthamido)benzyl]-1H-indazol-3-yl]acetic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[1-[4-(6-fluoro-2-naphthamido)benzyl]-1H-indazol-3-yl]acetate (262 mg, 0.544 mmol) was dissolved in tetrahydrofuran (10 mL), and in an ice bath 10 mL aqueous solution dissolving lithium hydroxide monohydrate (114 mg, 2.71 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 228 mg, at a yield of 92.5%.

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-d320eb041a054e068484b3a80c294109
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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