Water → ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetate

HRID 589359Notes

Reaction equation

HRID 589359 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.O>ClCCl>[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=3)=[CH:22][CH:23]=2)=[O:37])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 89590284ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetate

Product 1

HCID 89590282ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetateYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

220 mg (0.711 mmol) ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetate was dissolved in 20 mL dichloromethane, and triethylamine 0.15 mL (1.08 mmol) was added. The system was placed in an ice bath, and 137 mg (0.78 mmol) p-chlorobenzoyl chloride was added slowly. Upon completion of addition, the reaction was monitored to be complete by TLC. Water was added, extracted with ethyl acetate, and separated by a preparative chromatography to obtain 100 mg a white solid, at a yield of 31.4%.

Workup

  1. customThe system was placed in an ice bath
  2. additionUpon completion of addition
  3. extractionextracted with ethyl acetate
  4. customseparated by a preparative chromatography

Sources & evidence

ORD record
ord-82a63f6be66c42cbb6d073073ac1af3c
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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