Trifluoroacetic acid → HCID 25265681, compound

HRID 1810097Notes

Reaction equation

HRID 1810097 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[CH:22][C:21]=2[C:34]#[N:35])[CH:15]=[CH:14]3)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][C:21]=2[C:34]#[N:35])[CH:15]=[CH:14]3)=[O:10])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68510552HCID 68510552, compound

Product 1

HCID 25265681HCID 25265681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-(5-((4-chlorophenethyl)carbamoyl)-1H-indol-1yl)-3cyanophenyl)acetate (0.043 g, 0.0837 mmol) in DCM (0.5 mL) was added TFA (0.50 mL, 6.49 mmol). The reaction mixture was stirred for 1 hour and then concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0.5% methanol/DCM with 0.5% AcOH to 5% methanol/DCM containing 0.5% AcOH to provide 2-(4-(5-((4-chlorophenethyl)carbamoyl)-1H-indol-1yl)-3-cyanophenyl)acetic acid as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.15 (s, 1H), 7.91 (s, 1H), 7.81 (d, J=7.7 Hz, 1H), 7.67 (d, J=8.6 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.56 (d, J=3.0 Hz, 1H), 7.24-7.34 (m, 5H), 6.84 (d, J=3.9 Hz, 1H), 3.83 (s, 2H), 3.62 (t, J=7.5 Hz, 2H), 2.93 (t, J=7.4 Hz, 2H), MS(APCI)=458.1(M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with a gradient of 0.5% methanol/DCM with 0.5% AcOH to 5% methanol/DCM containing 0.5% AcOH

Sources & evidence

ORD record
ord-4cf6d8cf08ea428d9110bba199f9df96
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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