Hydrochloric Acid → HCID 11553248, compound

HRID 1821653Notes

Reaction equation

HRID 1821653 reaction equation
C(=[N:14][C:15]1[CH:43]=[CH:42][C:18]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([C:29]4[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=4)=[CH:27][N:28]=[C:23]3[NH:22][C:21]2=[O:41])=[CH:17][CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C1COCC1>[NH2:14][C:15]1[CH:43]=[CH:42][C:18]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([C:29]4[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=4)=[CH:27][N:28]=[C:23]3[NH:22][C:21]2=[O:41])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57893435HCID 57893435, compound

Product 1

HCID 11553248HCID 11553248, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(Benzhydrylideneamino)benzyl]-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one (10 mg, 0.0175 mmol) was dissolved in THF (0.5 mL) and 4N aq. HCl (0.3 mL) was added. The mixture was stirred overnight at room temperature, concentrated under reduced pressure, and the resultant residue was purified by silica gel chromatography [EtOAc] to afford 1-(4-aminobenzyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one (1.8 mg, 20% overall yield) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.90 (br, 1H), 8.32 (s, 1H), 7.40 (d, J=8.1 Hz, 2H), 7.19 (s, 2H), 6.62 (d, J=8.1 Hz, 2H), 5.08 (s, 2H), 3.99 (s, 6H), 3.92 (s, 3H). MS: 408.1 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe resultant residue was purified by silica gel chromatography [EtOAc]

Sources & evidence

ORD record
ord-dbf2cc3846ec49399006409c3f4f21f4
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

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