3-Furanol, tetrahydro- → HCID 57698403, compound

HRID 333695Notes

Reaction equation

HRID 333695 reaction equation
Br[C:2]1[C:3]([C:20]#[N:21])=[N:4][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:7]=1.[OH:22][CH:23]1[CH2:27][CH2:26][O:25][CH2:24]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[CH:17]1([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([C:8]([C:5]3[N:4]=[C:3]([C:20]#[N:21])[C:2]([O:22][CH:23]4[CH2:27][CH2:26][O:25][CH2:24]4)=[CH:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 10796Cesium carbonateHCID 57425300HCID 57425300, compound

Product 1

HCID 57698403HCID 57698403, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-6-(4-cyclopropyl-[1,4]diazepane-1-carbonyl)-pyridine-2-carbonitrile (0.600 g, 1.71 mmol), 3-hydroxytetrahydrofuran (301 mg, 3.41 mmol), and anhydrous Cs2CO3 (1.67 g, 5.13 mmol) in DMSO (7 mL) was heated by microwave irradiation at 150° C. for 35 min. The mixture was diluted with water and extracted with Et2O. The combined organic layers were dried (Na2CO3) and concentrated. The residue was purified by FCC to give the title compound (280 mg, 46%). MS (ESI): mass calcd. for C19H24N4O3, 356.4; m/z found, 357.5 [M+H]+. 1H NMR (CDCl3): 7.94 (d, J=8.8 Hz, 1H), 7.35 (d, J=8.9 Hz, 1H), 5.08-5.04 (m, 1H), 4.12-3.93 (m, 4H), 3.77-3.72 (m, 2H), 3.69-3.63 (m, 2H), 2.98-2.92 (m, 2H), 2.87-2.81 (m, 2H), 2.35-2.25 (m, 1H), 2.25-2.18 (m, 1H), 1.97-1.83 (m, 3H), 0.51-0.35 (m, 4H).

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe combined organic layers were dried (Na2CO3)
  3. concentrationconcentrated
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-88356812f4454cf0987c4d347827e234
Source dataset
uspto-grants-2014_11
Patent number
US08883776B2

Reaction notes

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