Water → HCID 71258388, compound

HRID 1506219Notes

Reaction equation

HRID 1506219 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[N:8]1[C:17]2[C:12](=[CH:13][N:14]=[C:15]3[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:18][C:16]3=2)[C:11](=[O:29])[CH:10]=[CH:9]1.C(N(CC)C(C)C)(C)C.[CH3:39][CH:40]([CH3:46])[CH2:41][S:42](Cl)(=[O:44])=[O:43].O>ClCCl>[CH2:41]([S:42]([N:5]1[CH2:6][CH2:7][C@@H:2]([CH3:1])[C@@H:3]([N:8]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]4[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:18][C:16]4=3)[C:11](=[O:29])[CH:10]=[CH:9]2)[CH2:4]1)(=[O:44])=[O:43])[CH:40]([CH3:46])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 71258404HCID 71258404, compound

Product 1

HCID 71258388HCID 71258388, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

rac-1-[(3R,4R)-4-Methylpiperidin-3-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (23 mg, 0.056 mmol) in dichloromethane (2 mL) was mixed with N,N-diisopropylethylamine (30 μL, 0.17 mmol) and 2-methylpropane-1-sulfonyl chloride (12 μL, 0.092 mmol) under cooling with ice and stirred at room temperature for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol=1/1/0→0/10/1 (v/v/v)) to give the title compound as a pale pink solid (18.3 mg, yield 62%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol=1/1/0→0/10/1 (v/v/v))

Sources & evidence

ORD record
ord-b7cbda1755ba43648d62bb10076f405b
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…