Lithium Hydroxide → HCID 11278675, compound

HRID 2242892Notes

Reaction equation

HRID 2242892 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:12]=[C:13]([NH2:25])[C:14]3[N:15]([N:17]=[C:18]([C:20]4[O:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH:16]=2)[CH:6]=1)C.[Li+].[OH-]>CO.C1COCC1>[NH2:25][C:13]1[C:14]2[N:15]([N:17]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:16]=[C:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:26])=[O:3])[N:12]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11268096HCID 11268096, compound

Product 1

HCID 11278675HCID 11278675, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture containing 3-(8-amino-2-furan-2yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid ethyl ester (100 mg; see Ex. 141 below, which was prepared according to Example 4 above), LiOH (2 M, 1 mL), and MeOH (a few drops) in THF (10 mL) was heated (at around 70° C.) for 1 hour. The solvent was removed in vacuo, and the residue was taken up in water and acidified, resulting in a precipitate, which was filtered off as the desired product with an appearance of a light brown solid (60 mg, 65 %). 1H NMR (300 MHz, DMSO-d6) δ 6.76 (dd, J=3.4, 1.8Hz, 1H), 7.18 (dd, J=3.4, 0.8, 1H), 7.63 (t, J=7.9 Hz, 1H), 7.68 (br. s, 2H), 7.96 (dd, J=1.8, 0.8 Hz, 1H), 8.00 (dt, J=7.8, 1.8 Hz, 1H), 8.30 (dt, J=7.8, 1.8 Hz, 1H), 8.72 (t, J=1.8, 1H), 8.91 (s, 1H), 13.09 (br. s, 1 H). MS: m/z 322 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customresulting in a precipitate, which
  3. filtrationwas filtered off as the desired product with an appearance of a light brown solid (60 mg, 65 %)

Sources & evidence

ORD record
ord-8b8b420fe05e452eb077800f0445ba1b
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

Loading…