HCID 70981446, compound → HCID 86724015, compound

HRID 1475424Notes

Reaction equation

HRID 1475424 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]3[O:22][N:21]=[C:20]([CH3:23])[N:19]=3)=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH3:25])([CH3:24])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH3:24])([CH3:25])[CH2:9][NH:8]2)=[CH:12][C:13]=1[C:18]1[O:22][N:21]=[C:20]([CH3:23])[N:19]=1

Participants

4

Reactant 1

HCID 70981446HCID 70981446, compound

Product 1

HCID 86724015HCID 86724015, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

6-Chloro-3,3-dimethyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (36 mg, 0.11 mmol) was dissolved in 50% TFA in DCM (0.534 mL) and the mixture was stirred for 30 minutes and concentrated. The residue was dissolved in methanol, loaded onto an SCX column and eluted with methanol then 2.0M ammonia in methanol to release the amine and fractions concentrated, to give the title compound (26 mg), MS: [M+H]+=264.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. washeluted with methanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14f86ac442fd48cda8cb70f215e0a914
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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