Diethylamine → HCID 54689853, compound

HRID 1244148Notes

Reaction equation

HRID 1244148 reaction equation
Br[C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(NCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([OH:53])(=[O:52])[CH2:46][CH2:47][CH2:48][CH2:49][C:50]#[CH:51]>CN(C=O)C.[Cu]I>[C:11]([C:8]1[C:7](=[O:13])[NH:6][C:5]2[S:14][C:2]([C:51]#[C:50][CH2:49][CH2:48][CH2:47][CH2:46][C:45]([OH:53])=[O:52])=[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[C:9]=1[OH:10])#[N:12]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 43779506-Heptynoic acidHCID 54689913HCID 54689913, compound

Product 1

HCID 54689853HCID 54689853, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Bromo-4-hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (150 mg, 0.45 mmol) in 4.5 mL DMF was added diethylamine (0.48 mL, 4.5 mmol), followed by copper(I) iodide (trace), Pd(PPh3)Cl2 (10 mg, 0.015 mmol), and triphenylphosphine (36 mg, 0.12 mmol). The resulting mixture was stirred at rt for 5 min, after which hept-6-ynoic acid (0.19 mL, 1.5 mmol) was added. The reaction was then heated to 120° C. using microwave for 25 min, filtered, concentrated and purified by reverse phase HPLC. MS (ESI) m/e 393 (M+H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 1.28–1.56 (m, 4H), 2.12–2.30 (m, 4H), 7.20–7.35 (m, 5H).

Workup

  1. temperatureThe reaction was then heated to 120° C.
  2. customfor 25 min
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-8dcc21fa6eed49f0ab444744e99a6015
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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