HCID 58378233, compound → HCID 44466645, compound

HRID 383465Notes

Reaction equation

HRID 383465 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)[C:9]3[C:14]([C:15]=2[NH:16][C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:28])[O:4][N:3]=1>I>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)[C:9]3[C:14]([C:15]=2[NH:16][C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

3

Reactant 1

HCID 58378233HCID 58378233, compound

Product 1

HCID 44466645HCID 44466645, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

1-(2-(3,5-Dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-1H-indol-3-yl)urea was heated neat in hydriodic acid (aq, 57%) at 100° C. for 3 hours. The reaction mixture was cooled and concentrated, and co-evaporated with DCM and EtOAc. The residue was subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by 1H NMR. ES/MS m/z: 363.19 (M+H), 362.18 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.65 (m, 1H), 7.22-7.09 (m, 5H), 6.93 (m, 2H), 2.25 (s, 3H) and 1.94 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customevaporated

Sources & evidence

ORD record
ord-681e104bc0744e2f9de466a4614123df
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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