Water → HCID 178505295, compound

HRID 1743785Notes

Reaction equation

HRID 1743785 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)=[N:6][CH:7]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].N1C(C)=CC=CC=1C.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][O:18][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:13][CH2:12]2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 178520940HCID 178520940, compound

Product 1

HCID 178505295HCID 178505295, compoundYield 161.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 481 mg (1.53 mmol) of trans-{4-[2-(5-Bromo-pyrimidin-2-ylamino)-ethyl]-cyclohexyl}-methanol in 14 ml CH2Cl2 was treated at 0 C with 0.13 ml (1.68 mmol) methanesulfonylchloride and 0.27 ml (2.30 mmol) 2,6-lutidine. The reaction was stirred for 20 h at room temperature, water (2 ml) was added and stirred for 5 min. After extraction with aqueous saturated NaHCO3/Et2O(3×), the organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 970 mg of crude trans-Methanesulfonic acid 4-[2-(5-bromo-pyrimidin-2-ylamino)-ethyl]-cyclohexylmethyl ester, MS: 392 (MH+, 1Br).

Workup

  1. stirringstirred for 5 min
  2. extractionAfter extraction with aqueous saturated NaHCO3/Et2O(3×)
  3. washthe organic phase was washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ebd7b79854234794b0bd460cb5bc9ad7
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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