Hydrochloric Acid → HCID 68665453, compound

HRID 640706Notes

Reaction equation

HRID 640706 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[C:11]4[CH2:19][CH2:18][O:17][C:16](=[O:20])[C:12]4=[N:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[OH-:23].[Na+].Cl>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3=[CH:14][N:13]=[C:12]([C:16]([OH:17])=[O:20])[C:11]([CH2:19][CH2:18][OH:23])=[C:10]3[CH:9]=[CH:8]2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53237707HCID 53237707, compound

Product 1

HCID 68665453HCID 68665453, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one (0.11 g, 0.37 mmol) in methanol (10 mL) was added sodium hydroxide (0.066 g, 1.65 mmol) in water (2.0 mL). The reaction was heated to 60° C. for 3 hours. After cooling down, the reaction mixture was neutralized with 4N hydrochloric acid (0.42 mL, 1.65 mmol). It was concentrated and dried in vacuo to provide the crude title compound as a white powder (0.11 g, 94%). 1H NMR (DMSO-d6) δ; 8.93 (d, 1H, J=1.9 Hz), 8.06 (s, 1H), 7.36 (m, 2H), 7.16 (t, 2H, J=6.6 Hz), 6.96 (s, 1H), 5.63 (s, 2H), 3.66 (t, 2H, J=6.8 Hz), 3.44 (t, 2H, J=6.8 Hz). LCMS (APCl, M+H+): 315.1.

Workup

  1. temperatureAfter cooling down
  2. concentrationIt was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-132470a0610e43e389ea1126543ac674
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

Loading…