Lithium Hydroxide → HCID 87604842, compound

HRID 1725987Notes

Reaction equation

HRID 1725987 reaction equation
[Br:1][C:2]1[C:3]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:19])=[O:18])=[C:4]([C:9]([O:14][CH3:15])=[C:10]([CH2:12][CH3:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].[OH-].[Li+].O1CCOCC1.C(#N)C>O>[Br:1][C:2]1[C:3]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:18])=[O:19])=[C:4]([C:9]([O:14][CH3:15])=[C:10]([CH2:12][CH3:13])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 312751,4-DioxaneHCID 87605505HCID 87605505, compound

Product 1

HCID 87604842HCID 87604842, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 470F (75 mg, 0.2 mmol), lithium hydroxide (70 mg, 2.0 mmol), dioxane (1.5 mL), and water (0.75 mL) was sealed in a vial and microwaved at 160° C. for 15 minutes. Purification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/10 mmol aqueous ammonium acetate over 8 minutes (10 minute run time) at a flow rate of 40 mL/min provided the desired compound. MS (ESI(+)) m/e 432, 434 (M+H)+; (ESI(−)) m/e 430, 432 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.68 (m, 1H), 7.57 (m, 1H), 7.28 (m, 3H), 3.65 (s, 3H), 2.49 (m, 4H), 1.09 (t, 3H).

Workup

  1. custommicrowaved at 160° C. for 15 minutes
  2. customPurification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  3. customover 8 minutes
  4. custom(10 minute run time)

Sources & evidence

ORD record
ord-da0347e914624c3b92fb58f1b3f80508
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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