Water → HCID 178482350, compound

HRID 1743769Notes

Reaction equation

HRID 1743769 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:19])[C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([N:8]([CH3:19])[C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]#[C:16][CH2:17][O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:13][CH2:14]2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178482349HCID 178482349, compound

Product 1

HCID 178482350HCID 178482350, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 420 mg (1.3 mmol) of trans-3-{4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-yn-1-ol in 10 ml CH2Cl2 was treated at 0° C. with 0.11 ml (1.43 mmol) methanesulfonylchloride, 0.16 ml (1.95 mmol) pyridine and 159 mg (1.3 mmol) DMAP. The reaction was stirred for 3.5 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 540 mg (quantitative) of trans-Methanesulfonic acid 3-{4-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-prop-2-ynyl ester, MS: 402 (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-6ce8faf3ffa3462f8a5ca7067e9c62d1
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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