Methanesulfonyl chloride → 3-(4-(4-cyano-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

HRID 2079555Notes

Reaction equation

HRID 2079555 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([C:18]#[N:19])[C:15]3[N:20]=[CH:21][N:22]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[C:14]=3[CH:13]=2)=[CH:8][C:7]=1[C:29]([F:32])([F:31])[F:30].CCN(C(C)C)C(C)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:42][S:43]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([C:18]#[N:19])[C:15]3[N:20]=[CH:21][N:22]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[C:14]=3[CH:13]=2)=[CH:8][C:7]=1[C:29]([F:31])([F:30])[F:32])(=[O:45])=[O:44]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 576575386-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 576575753-(4-(4-cyano-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (670 mg) and DIPEA (1.4 ml) in NMP (7.5 ml) at 0° C. was added methanesulphonyl chloride (0.2 ml). The mixture was allowed to stir for 45 minutes at room temperature, then diluted with EtOAc (75 ml) and washed with saturated sodium bicarbonate (70 ml), followed by water (2×40 ml). Organic layer was dried over sodium sulphate and solvent was evaporated under reduced pressure to yield 3-(4-(4-cyano-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate (720 mg).

Workup

  1. washwashed with saturated sodium bicarbonate (70 ml)
  2. dry with materialOrganic layer was dried over sodium sulphate and solvent
  3. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-11f7150b347240caaf7a4f8dc29fedf4
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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