Sulfuric Acid → HCID 71611596, compound

HRID 1774540Notes

Reaction equation

HRID 1774540 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=3[C:25]#[N:26])[C:15]([O:27][CH3:28])=[CH:14][N:13]=2)=[N:6]1.S(=O)(=O)(O)[OH:34].[OH-].[Na+]>>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=3[C:25]([NH2:26])=[O:34])[C:15]([O:27][CH3:28])=[CH:14][N:13]=2)=[N:6]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 71611319HCID 71611319, compound

Product 1

HCID 71611596HCID 71611596, compound

Procedure

To 126 mg of 4-({2-[1-(2-fluorobenzyl)-5-methoxy-1H-pyrazol-3-yl]-5-methoxypyrimidin-4-yl}amino)pyridine-3-carbonitrile 2-1-7 (0.294 mmol, 1.0 eq.) were given at rt with caution 0.446 mL of sulfuric acid. The mixture was stirred for 24 hours at rt. Then the reaction mixture was dropped into ice water and set with aqueous 2 M sodium hydroxide solution to an alkaline pH. This aqueous layer was extracted three times with DCM/propan-2-ol 4:1. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crystallization from methanol provided 37.0 mg (0.08 mmol, 28%) of analytically pure target compound.

Workup

  1. extractionThis aqueous layer was extracted three times with DCM/propan-2-ol 4:1
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crystallization from methanol
  5. customprovided 37.0 mg (0.08 mmol, 28%) of analytically pure target compound

Sources & evidence

ORD record
ord-94ed486bd9a841d3942519a1c45be665
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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