Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate → 7-(4-(5-Chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid

HRID 1626390Notes

Reaction equation

HRID 1626390 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:36]=[CH:35][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28]C(C)(C)C)=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:33]#[N:34])=[CH:13][CH:12]=2)=[O:10])=[N:6][CH:7]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:33]#[N:34])=[CH:35][CH:36]=2)=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 67288859Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate

Product 1

HCID 467015007-(4-(5-Chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acidYield 70.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (4 mg, 0.0079 mmol) was diluted with DCM (500 μL) and TFA (500 μL). After stirring for 2 hours, the reaction was concentrated and placed under high vacuum for 1 hour. The residue was purified by preparative TLC, eluting with 10% methanol/DCM to provide the desired product (2.5 mg, 0.0056 mmol, 70% yield) as a white solid. MS (ESI)=450.1 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. waitplaced under high vacuum for 1 hour
  3. customThe residue was purified by preparative TLC
  4. washeluting with 10% methanol/DCM

Sources & evidence

ORD record
ord-b87a450f447647dca4266c90e1af81f7
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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