(+/-)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoxaline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one → HCID 86629745, compound

HRID 551103Notes

Reaction equation

HRID 551103 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[C:8]3[CH2:24][C:14]4([C:22]5[C:17](=[N:18][CH:19]=[CH:20][CH:21]=5)[NH:16][C:15]4=[O:23])[CH2:13][C:9]3=[CH:10][C:11]=2[N:12]=1>C(Cl)(Cl)Cl.CO.[O-2].[Mn+4].[O-2]>[O:23]=[C:15]1[NH:16][C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:22]2[C:14]21[CH2:13][C:9]1=[CH:10][C:11]3[N:12]=[C:3]([CH:2]=[O:1])[CH:4]=[N:5][C:6]=3[CH:7]=[C:8]1[CH2:24]2

Participants

5

Reactant 1

HCID 67173211(+/-)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoxaline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 86629745HCID 86629745, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of (±)-2-(hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoxaline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (35 mg, 0.11 mmol) and manganese (IV) oxide (158 mg, 1.82 mmol) in CHCl3 (5 mL) and MeOH (0.1 mL) was heated at reflux for 18 h. The cooled mixture was filtered through a pad of Celite, washing with CH2Cl2 and MeOH, and the filtrate was concentrated in vacuo to give the title compound. MS: m/z=358 (M+1+CH3CN).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. filtrationThe cooled mixture was filtered through a pad of Celite
  4. washwashing with CH2Cl2 and MeOH
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-abe0e48ad19a4f7d87c5af03e24de05b
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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