Water → HCID 178482151, compound

HRID 1743782Notes

Reaction equation

HRID 1743782 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:20])[C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]#[C:17][CH2:18][OH:19])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C(C)=CC=CC=1C.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:20])[C@H:9]2[CH2:10][CH2:11][C@H:12]([CH2:15][C:16]#[C:17][CH2:18][O:19][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 178482150HCID 178482150, compound

Product 1

HCID 178482151HCID 178482151, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.08 g (3.68 mmol) of trans-4-{4-[(6-Chloro-pyridazin-3-yl)-methyl-amino]-cyclohexyl}-but-2-yn-1-ol in 30 ml CH2Cl2 was treated at 0° C. with 0.31 ml (4.04 mmol) methanesulfonylchloride and 0.64 ml (5.51 mmol) 2,6-lutidine. The reaction was stirred for 46 h at room temperature, water (4 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 1.45 g of crude trans-Methanesulfonic acid 4-{4-[(6-chloro-pyridazin-3-yl)-methyl-amino]-cyclohexyl}-but-2-ynyl ester, MS: 372 (MH+, 1Cl).

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-98ac12727cca4176a09373bfee0f60ac
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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