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Water → 3-chloromethyl-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-benzamide

HRID 1803853
Notes
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Reaction equation

HRID 1803853 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH2:16].[Cl:21][CH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27].O>CC1C=C(C)N=C(C)C=1>[Cl:21][CH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH2:5][C:4]3[CH:17]=[C:18]([F:20])[CH:19]=[C:2]([F:1])[CH:3]=3)[CH:8]=2)[NH:12][N:11]=1)=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 669970485-[(3,5-difluorobenzyl)oxy]-1H-indazol-3-amine

Product 1

HCID 462448313-chloromethyl-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-benzamideYield 56%

Reagents, catalysts & solvents 1

HCID 79532,4,6-Trimethylpyridine
Solvent

Conditions

Temperature
4 °C

Procedure

5-(3,5-Difluoro-benzyloxy)-1H-indazol-3-ylamine (550 mg, 2 mmol) was dissolved in sym-collidine, cooled to 4° C. and treated with neat 3-chloromethyl-benzoyl chloride (0.34 mL, 2.4 mmol). After 1 hour the reaction mixture was added drop wise into iced water, with stirring and separation of a yellow oil occurred. Then, EtOAc (50 mL) and 2N HCl (25 mL) were added. The organic phase was separated, washed with aqueous NaHCO3 (50 mL), brine, dried over sodium sulfate and evaporated to dryness. After purification over silica gel (eluent: DCM:MeOH 95:5) 378 mg of title compound were obtained as a whitish solid in 56% yield.

Workup

  1. customseparation of a yellow oil
  2. additionThen, EtOAc (50 mL) and 2N HCl (25 mL) were added
  3. customThe organic phase was separated
  4. washwashed with aqueous NaHCO3 (50 mL), brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customAfter purification over silica gel (eluent: DCM:MeOH 95:5) 378 mg of title compound
  8. customwere obtained as a whitish solid in 56% yield

Sources & evidence

ORD record
ord-f75a9373fc1446e1beb6364fdd07b40d
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354399B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes