HCID 68604082, compound → HCID 59370343, compound

HRID 1848636Notes

Reaction equation

HRID 1848636 reaction equation
C([O:5][C:6](=[O:41])[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:40])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]2[C:36]([C:37]#[N:38])=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[F:39])[N:28]=2)[CH:21]=1)[CH3:18])(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[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:41])=[O:5])=[O:40])=[CH:21][C:22]=1[C:27]1[C:36]([C:37]#[N:38])=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][C:33]=2[F:39])[N:28]=1

Participants

4

Reactant 1

HCID 68604082HCID 68604082, compound

Product 1

HCID 59370343HCID 59370343, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2-{[4-Chloro-3-(3-cyano-5-fluoro-quinolin-2-yl)-benzoyl]-methyl-amino}-phenoxy)-butyric acid tert-butyl ester (80.2 mg) was stirred in 50% trifluoroacetic acid in dichloromethane (2 mL) for 2 hrs and purified via reverse phase preparative LCMS to afford 4-(2-{[4-chloro-3-(3-cyano-5-fluoro-quinolin-2-yl)-benzoyl]-methyl-amino}-phenoxy)-butyric acid 33-1 (22.9 mg). MS [M+H]+: 518.4; tR=3.47 min. (method 3)

Workup

  1. custompurified via reverse phase preparative LCMS

Sources & evidence

ORD record
ord-ecc1a7fd5135492e8406449a80d27dfe
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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