Sodium Hydroxide → HCID 24874863, compound

HRID 2264773Notes

Reaction equation

HRID 2264773 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:21]2[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=2)([C:13]2[CH:18]=[C:17]([Cl:19])[N:16]=[C:15]([Cl:20])[CH:14]=2)[N:5]=1.[Cl:28][C:29]1[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[C:30]=1[S:36](Cl)(=[O:38])=[O:37]>O1CCCC1>[Cl:28][C:29]1[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[C:30]=1[S:36]([O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:6]2([C:13]3[CH:14]=[C:15]([Cl:20])[N:16]=[C:17]([Cl:19])[CH:18]=3)[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([NH2:3])=[N:5]2)[CH:22]=1)(=[O:37])=[O:38]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27771265-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 59596250HCID 59596250, compound

Product 1

HCID 24874863HCID 24874863, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (2.0 M, 0.559 ml, 1.12 mmol) was added to a solution of 3-(3-amino-1-(2,6-dichloropyridin-4-yl)-1H-isoindol-1-yl)phenol (Scheme #19, D, 0.069 g, 0.19 mmol) in tetrahydrofuran (1 mL) at 0° C. 5-Chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride (0.051 g, 0.22 mmol) was then added to the reaction mixture. After 30 minutes the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. Purification by flash chromatography using ethyl acetate followed by purification using preparative HPLC afforded 0.029 g (28% yield) of the title compound. 1H NMR (DMSO-d6) δ 7.87-7.77 (m, 2 H), 7.56-7.48 (m, 2 H), 7.41-7.34 (m, 2 H), 7.29 (s, 2 H), 7.12-7.01 (m, 3 H), 6.91 (d, J=1.77 Hz, 1 H), 3.74 (s, 3 H), 1.89 (s, 3 H); MS (AP) m/z 562 [M+1]+.

Workup

  1. customAfter 30 minutes the reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customPurification by flash chromatography
  6. customfollowed by purification

Sources & evidence

ORD record
ord-8e84b777bae145f7831168f4f3c6d5f5
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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