Hydrochloric Acid → HCID 136373242, compound

HRID 1014733Notes

Reaction equation

HRID 1014733 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.OC1C=CC(C2N=C3N(CC4CCCN4C(OC(C)(C)C)=O)C(=O)NC3=NC=2)=CC=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 136373241HCID 136373241, compoundHCID 136414662HCID 136414662, 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-((6-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)methyl)pyrrolidine-1-carboxylate (0.21 g., 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-7844785217f54d3da71f5e93bf7b55e3
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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