Water → HCID 86726642, compound

HRID 1506247Notes

Reaction equation

HRID 1506247 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:12]3[C:13]4[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]=4[N:15]=[CH:16][C:11]=3[CH2:10][NH:9][C:8]2=[O:28])[CH2:3][CH2:2]1.[C:29]1([CH2:35][S:36](Cl)(=[O:38])=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.O>ClCCl>[CH2:35]([S:36]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:12]3[C:13]4[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[C:14]=4[N:15]=[CH:16][C:11]=3[CH2:10][NH:9][C:8]2=[O:28])[CH2:5][CH2:6]1)(=[O:38])=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 71264278HCID 71264278, compound

Product 1

HCID 86726642HCID 86726642, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(Piperidin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-3,4-dihydro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-2(7H)-one (18.5 mg, 0.0460 mmol) in dichloromethane was mixed with phenylmethanesulfonyl chloride (17.5 mg, 0.092 mmol) and triethylamine (12.8 μL, 0.0920 mmol) for 1 hour under cooling with ice. After addition of water, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1 (v/v)) to give the title compound as a pale yellow solid (18.4 mg, yield 72%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=9/1 (v/v))

Sources & evidence

ORD record
ord-1702c98d14eb481ca77525d746fc573a
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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