Methanesulfonyl chloride → HCID 53247484, compound

HRID 527499Notes

Reaction equation

HRID 527499 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:34])[N:10]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=3)[CH2:16][N:15]([C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:27])[CH2:14]2)[CH2:11][CH3:12])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[S:44](Cl)([CH3:47])(=[O:46])=[O:45]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:34])[N:10]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=3)[CH2:16][N:15]([C:26]([CH:28]3[CH2:33][CH2:32][N:31]([S:44]([CH3:47])(=[O:46])=[O:45])[CH2:30][CH2:29]3)=[O:27])[CH2:14]2)[CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 53246744HCID 53246744, compound

Product 1

HCID 53247484HCID 53247484, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 32 mg (0.065 mmol) [(3S,4R)-4-(4-Chloro-3-fluoro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid 4-fluoro-phenyl ester, 57 uL (0.325 mmol) DIPEA and 11.2 mg (0.097 mmol) mesyl chloride in 1.5 mL DMF was shaken for 90 min at room temperature. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 16 mg (43%) of the title compound as off-white solid. MS m/e: 570.4 [M+11]+.

Workup

  1. customThe mixture was subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. additionThe product containing fractions
  5. customwere evaporated

Sources & evidence

ORD record
ord-b64083b4ba9845619ab4ce656851d5bc
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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