Indole → HCID 10791428, compound

HRID 984477Notes

Reaction equation

HRID 984477 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[S:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]3)=[O:22])=[CH:15][C:14]=2[Cl:32])[CH:5]=[CH:4]1)C.[NH:33]1C2C(=CC=CC=2)C=[CH:34]1.[C:42](O)(C(F)(F)F)=O>CO>[CH3:1][N:3]([CH2:4][C:5]1[C:6]2[C:7](=[CH:8][CH:9]=[C:10]([S:12][C:13]3[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([N:23]4[CH2:24][CH2:25][N:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]4)=[O:22])=[CH:15][C:14]=3[Cl:32])[CH:11]=2)[NH:33][CH:34]=1)[CH3:42]

Participants

5

Reactant 3

HCID 798IndoleHCID 6422Trifluoroacetic acidHCID 10479728HCID 10479728, compound

Product 1

HCID 10791428HCID 10791428, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by the procedures described in Example 217, substituting the indole from Example 186 with the indole from Example 85, resulting in a white solid. 1H NMR (CDCl3, 300 MHz) δ 2.15 (s, 3H), 2.54 (s, 6H), 3.47-3.85 (m, 8H), 4.05 (s, 2H), 6.56 (d, J=8.7 Hz, 1H), 6.77 (d, J=15.6 Hz, 1H), 7.09 (d, J=8.7 Hz, 1H), 7.36 (dd, J=1.5, 8.7 Hz, 1H), 7.50 (d, J=8.7 Hz, 1H), 7.52 (s, 2H), 7.56 (d, J=15.6 Hz, 1H), 7.88 (s, 1H), 9.27 (s, 1H). MS (ESI+) (M+H)+ at m/z 497, 499. Anal. Calcd for C26H29ClN4O2S.0.46 TFA.1.72 MeOH: C, 56.89; H, 6.06; N, 9.27. Found: C, 56.83; H, 6.15; N, 9.46.

Workup

  1. customresulting in a white solid

Sources & evidence

ORD record
ord-7ee9fee401fd49f8a05fe559cd0f6aae
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

Loading…