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Hydrochloric Acid → 6-[3-({[3-(1-Cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazole-7-carboxylic acid

HRID 455234
Notes
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Reaction equation

HRID 455234 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:38]=[CH:39][CH:40]=2)[O:18][C:19]2[CH:33]=[CH:32][C:22]3[N:23]=[C:24]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[S:25][C:21]=3[C:20]=2[C:34]([O:36]C)=[O:35])=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2].O.[OH-].[Li+].Cl>O1CCCC1.CO.O.C(OCC)(=O)C>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:38]=[CH:39][CH:40]=2)[O:18][C:19]2[CH:33]=[CH:32][C:22]3[N:23]=[C:24]([NH:26][C:27]([CH:29]4[CH2:30][CH2:31]4)=[O:28])[S:25][C:21]=3[C:20]=2[C:34]([OH:36])=[O:35])=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59454479Methyl 6-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazole-7-carboxylate

Product 1

HCID 594544926-[3-({[3-(1-Cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazole-7-carboxylic acidYield 54.4%

Reagents, catalysts & solvents

4
HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazole-7-carboxylate (570 mg, 1.02 mmol) produced in Example 46(iv) was dissolved in a mixed solvent of tetrahydrofuran (6 mL)/methanol (2 mL)/water (2 mL), lithium hydroxide monohydrate (150 mg, 3.66 mmol) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was neutralized with 1N hydrochloric acid, diluted with ethyl acetate (100 mL)/tetrahydrofuran (100 mL) and washed with water (100 mL). The organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (300 mg, 54%) as a white powder.

Workup

  1. additionwas added
  2. washwashed with water (100 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90)
  5. concentrationthe obtained solution was concentrated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-96c7eb76fc824dcb982f4808ee1be398
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497274B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes