HCID 58215605, compound → HCID 58215753, compound

HRID 1661575Notes

Reaction equation

HRID 1661575 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[C:11]([C:13]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]#[N:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:14])[CH:10]=[CH:9][C:8]=1[CH3:32])(C)(C)C>FC(F)(F)C(O)=O>[C:24]([C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:15]([C:13]([C:11]1[CH:10]=[CH:9][C:8]([CH3:32])=[C:7]([CH:12]=1)[C:6]([OH:33])=[O:5])=[O:14])[C:16]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[CH:17]2)#[N:25]

Participants

3

Reactant 1

HCID 58215605HCID 58215605, compound

Product 1

HCID 58215753HCID 58215753, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-2-methyl-benzoic acid tert-butyl ester is dissolved in trifluoroacetic acid (3 mL), and stirred at room temperature for 1 h. After removing the solvent, the residue is purified by HPLC with an X-bridge Phenyl using acetonitrile-0.1% trifluoroacetic acid as an eluent to yield 5-(5-cyano-2-pyridin-3-yl-indole-1-carbonyl)-2-methyl-benzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm (TFA salt) 2.59 (s, 3H), 7.32 (s, 1H), 7.39-7.44 (m, 2H), 7.71-7.75 (m, 1H), 7.76-7.79 (m, 1H), 7.81 (dd, J=7.8, 2.0 Hz, 1H), 7.92 (dt, J=8.0, 1.8 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 8.38 (d, J=1.5 Hz, 1H), 8.52 (dd, J=5.0, 1.5 Hz, 1H), 8.74 (d, J=2.0 Hz, 1H). HRMS (ESI) m/z 382.1202 [(M+H)+ Calcd for C23H16N3O3: 382.1192].

Workup

  1. customAfter removing the solvent
  2. customthe residue is purified by HPLC with an X-bridge Phenyl

Sources & evidence

ORD record
ord-e97782df397c45238d3da65cf724e032
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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