Sodium Hydroxide → HCID 59727115, compound

HRID 1363201Notes

Reaction equation

HRID 1363201 reaction equation
[N:1]1([C:10]2[N:18]=[C:17]3[C:13]([NH:14][C:15](=[O:37])[N:16]3[CH:19]3[CH2:27][CH2:26][CH2:25][C:24]4[N:23](S(C5C=CC=CC=5)(=O)=O)[CH:22]=[CH:21][C:20]3=4)=[CH:12][N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+]>CO>[N:1]1([C:10]2[N:18]=[C:17]3[C:13]([NH:14][C:15](=[O:37])[N:16]3[CH:19]3[CH2:27][CH2:26][CH2:25][C:24]4[NH:23][CH:22]=[CH:21][C:20]3=4)=[CH:12][N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59726925HCID 59726925, compound

Product 1

HCID 59727115HCID 59727115, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(1H-benzo[d]imidazol-1-yl)-9-(1-(phenylsulfonyl)-4,5,6,7-tetrahydro-1H-indol-4-yl)-7H-purin-8(9H)-one (50 mg) in MeOH (1 mL) was added 4 N NaOH (1 mL), and the mixture was refluxed overnight and cooled. Volatiles were removed under reduced pressure, and the resultant neutralized with 4 N HCl. The white precipitate was filtered, washed with a small amount of water, and dried in vacuo to afford 36 mg of the title compound. 1H NMR (d6-DMSO) δ 11.6 (s, 1H), 10.7 (s, 1H), 8.86 (s, 1H), 8.27 (s, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.33 (m, 2H), 6.53 (t, J=2.4 Hz, 1H), 5.64 (t, J=2.4 Hz, 1H), 5.54 (m, 1H), 2.72 (m, 2H), 2.30 (m, 1H), 2.07 (m, 2H), 1.84 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperaturecooled
  3. customVolatiles were removed under reduced pressure
  4. filtrationThe white precipitate was filtered
  5. washwashed with a small amount of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3980bd682e754c4d9b84689c15aa125d
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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