Methanesulfonyl chloride → HCID 178505157, compound

HRID 1403155Notes

Reaction equation

HRID 1403155 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][C:14]3[CH:19]=[C:18]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=[C:21]4[CH:29]([F:31])[F:30])[N:17]=[C:16]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[N:15]=3)[CH2:9][CH2:8]2)[C:3]1=[O:38].C(N(C(C)C)C(C)C)C.[CH3:48][S:49](Cl)(=[O:51])=[O:50].C(=O)(O)[O-].[Na+]>ClCCCl>[F:30][CH:29]([F:31])[C:21]1[N:20]([C:18]2[N:17]=[C:16]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[N:15]=[C:14]([O:13][C@H:10]3[CH2:11][CH2:12][C@H:7]([N:4]4[CH2:5][CH2:6][C@H:2]([NH:1][S:49]([CH3:48])(=[O:51])=[O:50])[C:3]4=[O:38])[CH2:8][CH2:9]3)[CH:19]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178511747HCID 178511747, compound

Product 1

HCID 178505157HCID 178505157, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To (3S)-3-amino-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]pyrrolidin-2-one (75 mg), N-ethyl-N-isopropylpropan-2-amine (73 μL), and 1,2-dichloroethane (750 μL) was added methanesulfonyl chloride (17 μL), followed by stirring at room temperature for 1 hour. After the completion of the reaction, a saturated aqueous sodium bicarbonate solution was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol) to obtain N-{(3S)-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]-2-oxopyrrolidin-3-yl}methanesulfonamide (82 mg) as a pale yellow powder.

Workup

  1. customAfter the completion of the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-921a74e3b1d747c18c90ae49054d3458
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…