Water → HCID 178426465, compound

HRID 1743770Notes

Reaction equation

HRID 1743770 reaction equation
[CH3:1][N:2]([C:13]1[N:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[C:10][CH2:11]O)[CH2:5][CH2:4]1.CS([Cl:24])(=O)=O.N1C(C)=CC=CC=1C.O>C(Cl)Cl>[Cl:24][CH2:11][C:10]#[C:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[C:13]2[N:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 178426466HCID 178426466, compound

Product 1

HCID 178426465HCID 178426465, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.246 g (0.95 mmol) of trans-3-{4-[Methyl-(6-methyl-pyridazin-3-yl)-amino]-cyclohexyl}-prop-2-yn-1-ol in 7 ml CH2Cl2 was treated at 0° C. with 0.081 ml (1.04 mmol) methanesulfonylchloride and 0.17 ml (1.42 mmol) 2,6-lutidine. The reaction was stirred for 22 h at room temperature, water (1 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 0.285 g of crude trans-[4-(3-Chloro-prop-1-ynyl)-cyclohexyl]-methyl-(6-methyl-pyridazin-3-yl)-amine, MS: 278 (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-87c748018a5c499ead27ada14a3c9ec5
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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