Methanesulfonyl chloride → HCID 58869557, compound

HRID 2233088Notes

Reaction equation

HRID 2233088 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[N:14][CH:13]=[CH:12][N:11]3[C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:18]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[N:14][CH:13]=[CH:12][N:11]3[C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]3[CH2:29][CH2:28][N:27]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:26][CH2:25]3)[N:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58869546HCID 58869546, compound

Product 1

HCID 58869557HCID 58869557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[2-(4-fluorophenyl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylpiperidin-4-ylamine (Example # H.1; 0.200 g, 0.514 mmol) and DIEA (0.18 mL, 1.0 mmol) in DCM (3 mL) at ambient temperature was added methanesulfonyl chloride (0.062 g, 0.539 mmol). After about six days, the mixture was treated with saturated aqueous NaHCO3 and the layers were separated. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude material was triturated with EtOAc and filtered to yield the title compound after drying (0.090 g, 37%): LC/MS (Table 1, Method b) Rt=1.7 min; MS m/z: 468.6 (M+H)+.

Workup

  1. customat ambient temperature
  2. customthe layers were separated
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was triturated with EtOAc
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a4db3d37c7864805a1a9d2bad800058e
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

Loading…