HCID 68602392, compound → HCID 59370352, compound

HRID 1485934Notes

Reaction equation

HRID 1485934 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]([C:19](=[O:36])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]2[CH:28]=[N:29][C:30]([C:34]#[N:35])=[CH:31][C:32]=2[CH3:33])[CH:21]=1)[CH3:18])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([N:17]([CH3:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7][C:6]([OH:37])=[O:5])=[O:36])=[CH:21][C:22]=1[C:27]1[CH:28]=[N:29][C:30]([C:34]#[N:35])=[CH:31][C:32]=1[CH3:33]

Participants

4

Reactant 1

HCID 68602392HCID 68602392, compound

Product 1

HCID 59370352HCID 59370352, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2-{[4-Chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-butyric acid tert-butyl ester (60 mg, 0.12 mmol) was stirred in a mixture of DCM (400 μL) and TFA (400 μL) for 1 hr. The mixture was concentrated, dissolved in MeOH and purified by prep LCMS to yield 4-(2-{[4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-butyric acid 5-1. MS [M+H]+: 463.7; tR=3.46 min, (method 2)

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in MeOH
  3. custompurified by prep LCMS

Sources & evidence

ORD record
ord-d79307e77a404aa28be08c090e548431
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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