Hydrochloric Acid → HCID 136373242, compound

HRID 388136Notes

Reaction equation

HRID 388136 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[N:15]([CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][NH:21]4)[C:16](=[O:18])[NH:17][C:12]3=[N:11][CH:10]=2)=[CH:5][CH:4]=1.Cl>O1CCOCC1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]3[N:15]([CH2:19][CH:20]4[CH2:24][CH2:23][CH2:22][NH:21]4)[C:16](=[O:18])[NH:17][C:12]3=[N:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136373241HCID 136373241, compound

Product 1

HCID 136373242HCID 136373242, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

6-(4-Hydroxyphenyl)-1-(pyrrolidin-2-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride. tert-Butyl 2-4-((6-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)methyl)pyrrolidine-1-carboxylate (0.21g., 0.52 mmol) was dissolved in 1,4-dioxane (3 mL), 1M hydrochloric acid in 1,4-dioxane (1 mL) was added and the mixture was stirred at rt for 48 h. The solvent was removed, the resulting residue was triturated with methanol and filtered to yield the title compound (0.11 g., 61% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.768 (s, 1H), 9.4 (bs,1H), 8.68 (bs, 1H), 8.415 (s, 1H), 7.906 (d, J=8.8, 2H), 6.873 (d, J=8.8, 2H), 4.19 (d, J=6.8, 2H), 3.89 (m, 1H), 3.30 (m, 1H), 3.13 (m, 1H), 2.14 (m, 1H), 1.97 (m, 2H), 1.79 (m, 1H); MS (ESI) m/z 312.1[M+1]+; mp 178-180° C.

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was triturated with methanol
  3. filtrationfiltered

Sources & evidence

ORD record
ord-98a6751f0e384b7d92a09385d7f705fd
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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