Lithium hydroxide, monohydrate → HCID 178525370, compound

HRID 1353784Notes

Reaction equation

HRID 1353784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[N:20][N:21]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[NH:18][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[N:20][N:21]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178471183HCID 178471183, compound

Product 1

HCID 178525370HCID 178525370, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask containing ethyl 3-{5-{3-(4-fluorophenyl)-1H-indazole-5-yl]-4H-1,2,4-triazol-3-yl}propanoate (37 mg, 0.1 mmol) was added lithium hydroxide monohydrate (8.2 mg, 0.2 mmol). This was taken up in tetrahydrofuran and allowed to stir under a nitrogen atmosphere overnight. The reaction was acidified slightly. The product was found to be soluble in both the aqueous and organic layers. The layers were concentrated and the product was purified by semipreparative HPLC (20–80% acetonitrile with 0.1% fonnic acid over 30 minutes). The fractions containing the compound were concentrated to yield the title compound (11 mg, 32% yield). 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 8.6 (s, 1H), 8.0 (m, 3H), 7.6 (d, 1H), 7.4 (t, 2H), 2.95 (m, 2H), 2.7 (m, 2H); ES-MS m/z 352 [M+H]+.

Workup

  1. concentrationThe layers were concentrated
  2. customthe product was purified by semipreparative HPLC (20–80% acetonitrile with 0.1% fonnic acid over 30 minutes)
  3. additionThe fractions containing the compound
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-6e27b1f47a7d4fc7838e9f4c10b64a26
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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