HCID 68602827, compound → HCID 59370369, compound

HRID 1485954Notes

Reaction equation

HRID 1485954 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]([C:18](=[O:38])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]2[C:35]([C:36]#[N:37])=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH:20]=1)[CH3:17])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:16]([CH3:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7][C:6]([OH:39])=[O:5])=[O:38])=[CH:20][C:21]=1[C:26]1[C:35]([C:36]#[N:37])=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1

Participants

4

Reactant 1

HCID 68602827HCID 68602827, compound

Product 1

HCID 59370369HCID 59370369, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2-{[4-Chloro-3-(3-cyano-quinolin-2-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid tert-butyl ester (20 mg, 0.037 mmol) was stirred in a mixture of DCM (0.2 mL) and TFA (0.2 mL) for 1 hr. The mixture was concentrated, dissolved in MeOH and purified by prep LCMS to yield 4-(2-{[4-chloro-3-(3-cyano-quinolin-2-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid 15-1. MS [M+H]+: 483.9; tR=7.05 min, (method 2)

Workup

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

Sources & evidence

ORD record
ord-4706ffa0b2da4233bb09fa304df8944d
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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