Hydrochloric Acid → HCID 66799955, compound

HRID 528016Notes

Reaction equation

HRID 528016 reaction equation
[OH-:1].[Na+].[CH3:3][N:4]1[C:13]2[N:12]=[CH:11][N:10]=[C:9]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:16][CH2:15]3)[C:8]=2[N:7]=[C:6](OC)[C:5]1=[O:32].Cl>CO>[CH3:3][N:4]1[C:6]([C:5]([OH:32])=[O:1])=[N:7][C:8]2[C:13]1=[N:12][CH:11]=[N:10][C:9]=2[N:14]1[CH2:15][CH2:16][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66799879HCID 66799879, compound

Product 1

HCID 66799955HCID 66799955, compoundYield 589.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methanol (25 mL) and aqueous 2M sodium hydroxide solution (25.4 mmol, 12.7 mL, 10 equiv) were added to 8-methyl-6-(methyloxy)-4-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]pteridin-7(8H)-one (1.00 g, 2.54 mmol, 1 equiv) in a 100 mL single-necked round bottomed flask fitted with a Teflon stirrer. The resulting stirred slurry was then heated to 80° C. and the reaction was monitored by LC/MS. The reaction mixture gradually became clear and homogenous. LC/MS indicated that the reaction was complete after 12 hours. The new product peak was characterized by a 394 (MH+) molecular ion and a 350 (MH+−44 (—CO2) decarboxylation fragmentation peak. The reaction mixture was then allowed to cool to room temperature. The stirred reaction mixture was then acidified to pH 2 by the gradual addition of aqueous 3M hydrochloric acid, resulting in the precipitation of a white solid. The resulting slurry was then stirred for 30 minutes and then filtered off. The solid was washed with cold water (2×10 mL) and dried at reduced pressure to give 5.89 g (82% yield) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.89 (broad s, 1H), 8.33 (s, 1H), 7.17 (dd, 1H), 6.91 (m, 3H), 5.40 (v broad s, 2H), 4.56 (t, 1H), 3.22 (broad s, 2H), 2.33 (d, 2H), 1.85 (d, 2H). MS (EI) for C18H17N7O3: 394 (MH+), 350 (MH+−44 (—CO2).

Workup

  1. customfitted with a Teflon stirrer
  2. temperatureto cool to room temperature
  3. customThe stirred reaction mixture
  4. customresulting in the precipitation of a white solid
  5. stirringThe resulting slurry was then stirred for 30 minutes
  6. filtrationfiltered off
  7. washThe solid was washed with cold water (2×10 mL)
  8. customdried at reduced pressure

Sources & evidence

ORD record
ord-51f0e08bfc1b42e3a392ef63f8d5c251
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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