Pyridine → HCID 76770966, compound

HRID 241628Notes

Reaction equation

HRID 241628 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:12]([C:13]2[N:14]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:15]3[C:20]([C:21]=2[C:22](=O)[C:23]([NH2:25])=[O:24])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:34])[O:10][N:9]=1.Cl.[NH2:36][OH:37]>CCO>[CH3:7][C:8]1[C:12]([C:13]2[N:14]([C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[C:15]3[C:20]([C:21]=2[C:22](=[N:36][OH:37])[C:23]([NH2:25])=[O:24])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:34])[O:10][N:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 44466648HCID 44466648, compound

Product 1

HCID 76770966HCID 76770966, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

50 μl Pyridine was added to 8.8 mg 2-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2-oxoacetamide and 32.6 mg hydroxylamine hydrochloride in 1.5 ml EtOH in a microwave vial. The vial was sealed and flushed with nitrogen. The mixture was heated to 150° C. for 7.5 min. and then to 150° C. for 5 min. in a Biotage Initiator microwave oven. The mixture was concentrated in vacuo and purified by preparative HPLC (formic acid buffer/acetonitrile). 2-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2(hydroxyimino)acetamide (E35) was obtained as a mixture of syn and anti oxime isomers. ES/MS m/z: 391.4 (M+H), 389.5 (M−H); 1H NMR (DMSO-d6, 500 MHz): 7.37 (m, 1H), 7.20-7.03 (m, 5H), 6.84 (m, 2H), 2.15 (s, 3H) and 1.77 (s, 3H).

Workup

  1. customThe vial was sealed
  2. customflushed with nitrogen
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by preparative HPLC (formic acid buffer/acetonitrile)

Sources & evidence

ORD record
ord-aab60d531e01476f99b1a15f0a9f4b34
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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