Sodium Hydroxide → HCID 57742685, compound

HRID 335227Notes

Reaction equation

HRID 335227 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH:15]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]3=[O:27])[N:13]=2)=[N:6][CH:7]=1.[OH-:35].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH:15]([CH2:19][CH2:18][NH:17][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:16]([OH:27])=[O:35])[N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86631526HCID 86631526, compound

Product 1

HCID 57742685HCID 57742685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

tert-Butyl 3-((2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)methyl)-2-oxopyrrolidine-1-carboxylate (0.070 g, 0.128 mmol) (Example 393, Steps A-C) was dissolved in 1 mL of THF and sodium hydroxide (0.963 mL, 1.93 mmol) 2M solution was added. The resulting solution was heated to 55° C. and agitated for 3 hours. Reaction was quenched with 3 mL of 2M potassium hydrosulfate solution and extracted twice with ethyl acetate. The extracts were washed with water, brine, dried and evaporated to produce the title compound. 1H NMR (CDCl3) δ 1.40 (s, 9H), 1.60-1.74 (m, 2H), 2.64-3.08 (m, 5H), 4.65 (bs, 1H), 6.47 (s, 1H), 7.09-7.43 (m, 7H), 8.14 (s, 1H).

Workup

  1. customReaction
  2. customwas quenched with 3 mL of 2M potassium hydrosulfate solution
  3. extractionextracted twice with ethyl acetate
  4. washThe extracts were washed with water, brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d4ef844a98224168b916ae42d750a690
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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