Water → HCID 56591988, compound

HRID 1616080Notes

Reaction equation

HRID 1616080 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[C:15]2[O:22][CH:21]=[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:16]=2[N:17]=[CH:18][N:19]=1.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].O>N1C=CC=CC=1.C(Cl)Cl>[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:10])=[O:11])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[C:15]2[O:22][CH:21]=[C:20]([CH:23]3[CH2:28][CH2:27][N:26]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH2:25][CH2:24]3)[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 86681873HCID 86681873, compound

Product 1

HCID 56591988HCID 56591988, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

N-[2-Fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (9.0 mg, 0.021 mmol) was dissolved in pyridine (0.4 mL), and a 0.25 mol/L solution of benzyl chloroformate in anhydrous methylene chloride (0.1 mL) was added dropwise slowly under ice-cooling, and then the resultant mixture was stirred for 15 minutes under ice-cooling, and water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=20:1) to give the titled compound (5.6 mg, 51%) as a yellow oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customthe obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-440d97badd994385bfbcfb090d0b6fc3
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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