N-methyl-2-pyrrolidone → HCID 67494458, compound

HRID 2047163Notes

Reaction equation

HRID 2047163 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=C[C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[NH:38]1[CH2:43][CH2:42][S:41](=O)(=O)[CH2:40][CH2:39]1.[C:46]([O-:49])(O)=O.[Na+].CN1C(=[O:57])CCC1>O>[S:41]1[CH2:42][CH2:43][N:38]([C:2]2[C:7](=[O:57])[CH:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:24])[CH3:23])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:14])[CH3:15])[N:5]3[NH:25][C:46](=[O:49])[C:27]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:4]3[N:3]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 6484228Thiomorpholine 1,1-dioxideHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Product 1

HCID 67494458HCID 67494458, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (503.0 mg, 0.91 mmoL), thiomorpholine 1,1-dioxide (367.1 mg, 2.72 mmoL), NaHCO3 (533.0 mg, 6.34 mmoL) in NMP (8 mL) was heated at 130° C. overnight. The mixture was cooled to room temperature and diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation of solvent afforded the crude displacement compound. Purification by column chromatography afforded compound 5-thiomorpholinodioxo-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine LCMS tR=2.52 Min (5 min run, UV254nm). Mass calculated for, M+ 654.2, observed m/z 655.2 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customEvaporation of solvent
  6. customafforded the crude displacement compound
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-fbe7ce9365844e0a92789481c7560a21
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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