Triethylamine → HCID 22027868, compound

HRID 1791133Notes

Reaction equation

HRID 1791133 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[Cl:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28]O)[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C>C1COCC1>[Cl:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([N:26]4[CH2:27][CH2:28][O:2][S:1]4=[O:3])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 19689608HCID 19689608, compound

Product 1

HCID 22027868HCID 22027868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sulfonyl chloride (0.63 g, 5.3 mmol) in THF (2 ml) is added within 5 minutes to a solution of 2-{4-(2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-ethanol (1.50 g, 4.4 mmol) and triethylamine (3.0 ml, 22 mmol) in absolute THF (20 ml) at +5° C. After stirring the resulting suspension for four hours at room temperature it is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography to give the title compound, m.p. 202–203° C.

Workup

  1. customis partitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced presssure
  6. customThe residue is purified by silicagel chromatography

Sources & evidence

ORD record
ord-71b823c546504e85b63e3a1e74f4dfa2
Source dataset
uspto-grants-2006_07
Patent number
US07074787B2

Reaction notes

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