Triethylamine → HCID 117840283, compound

HRID 714874Notes

Reaction equation

HRID 714874 reaction equation
[CH2:1]([C@:3]1([C:28]#[N:29])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)[C:4]1=[O:27])[CH3:2].C(N(CC)CC)C.[CH3:37][S:38]([Cl:41])(=[O:40])=[O:39].[Cl-].[NH4+]>O1CCCC1>[ClH:41].[CH2:1]([C@:3]1([C:28]#[N:29])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:26][CH2:25][N:24]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:23][CH2:22]4)=[CH:19][CH:20]=3)[N:9]=2)[C:4]1=[O:27])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 89863359HCID 89863359, compound

Product 1

HCID 117840283HCID 117840283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R)-3-ethyl-2-oxo-1-(2-((4-(piperazin-1-yl)phenyl)amino)pyrimidin-4-yl)pyrrolidine-3-carbonitrile (100 mg) obtained in Example 220 in tetrahydrofuran (3.0 mL) were added successively dropwise triethylamine (71 μL) and methanesulfonyl chloride (24 μL) in an ice bath, and the mixture was stirred at the same temperature for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), to a solution of the obtained purified product (120 mg) in ethanol (3 mL) was added 1 M hydrochloric acid (0.25 mL), and the mixture was stirred at room temperature for 5 min. The solvent was evaporated under reduced pressure, and the residue was recrystallized (ethanol/diisopropyl ether) to give the title compound (91 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate), to a solution of the obtained
  3. custompurified product (120 mg) in ethanol (3 mL)
  4. additionwas added 1 M hydrochloric acid (0.25 mL)
  5. stirringthe mixture was stirred at room temperature for 5 min
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was recrystallized (ethanol/diisopropyl ether)

Sources & evidence

ORD record
ord-a7ca001348ca411cb7e30c2388fe55c8
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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