Quinoline → HCID 10237225, compound

HRID 2307758Notes

Reaction equation

HRID 2307758 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH2:28])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:19]=2)=[CH:2]1.N1C2C(=CC=CC=2)C=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH2:28])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18](/[CH:20]=[CH:21]\[C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH:19]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 10237197HCID 10237197, compound

Product 1

HCID 10237225HCID 10237225, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 14D (40 mg, 0.11 mmol), 5% Pd/BaSO4 (8.1 mg) and quinoline (8.1 μL) in methanol (3 mL) was stirred under hydrogen (20 psi) at room temperature for 12 minutes and filtered. The filtrate was concentrated and the residual oil was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA to provide the desired product (30 mg, 75%). MS (APCI) m/e 369 (M−H)−; 1H NMR (300 MHz, CD3OD) δ 8.57 (d, J=6.8 Hz, 2H), 8.29 (d, J=2.4 Hz, 1H), 8.04 (s, 1H), 7.69 (d, J=6.4 Hz, 2H), 7.57 (d, J=7.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.33 (t, J=1.7 Hz, 1H), 7.21 (s, 1H), 7.14 (m, 2H), 7.02 (td, J=8.1, 1.0 Hz, 1H), 6.95 (d, J=12.2 Hz, 1H), 4.24 (dd, J=10.5, 3.0 Hz, 1H), 4.08 (dd, J=10.5, 5.6 Hz, 1H), 3.92 (m, 1H), 3.26 (m, 2H); Anal. Calcd for C23H22N4O. 3.6 TFA: C, 46.45; H, 3.30; N, 7.17. Found: C, 46.56; H, 3.35; N, 7.34.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residual oil was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA

Sources & evidence

ORD record
ord-d03902449807401c8c76ea1f21a9defb
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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