Ammonia → HCID 16752727, compound

HRID 2194995Notes

Reaction equation

HRID 2194995 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=1.[CH3:26][NH:27][CH2:28][C:29]#[CH:30].C(N(C(C)C)CC)(C)C.O=O.N>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:30]#[C:29][CH2:28][NH:27][CH3:26])=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 977OxygenHCID 81531DiisopropylethylamineHCID 96160N-methylpropyn-2-ylamineHCID 59254920HCID 59254920, compound

Product 1

HCID 16752727HCID 16752727, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g (2.1 mmol) N-[8-(2-chloro-5-iod-phenyl)-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl]-acetamide are placed in 50 mL tetrahydrofuran under an argon atmosphere and combined with 0.6 ml (9 mmol) N-methylpropargylamine and 1 mL (6 mmol) diisopropylethylamine. The mixture is kept free from oxygen and 29 mg (0.04 mmol) triphenylphosphine palladium(II)-chloride and 8 mg (0.04 mmol) copper(I)-iodide are added. The mixture is stirred for 5 hours at 80° C. After cooling to ambient temperature the reaction mixture is combined with water and 10% ammonia solution and extracted with dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography, the product obtained is triturated with diethyl ether and suction filtered.

Workup

  1. additionare added
  2. temperatureAfter cooling to ambient temperature the reaction mixture
  3. extractionextracted with dichloromethane
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography
  7. customthe product obtained
  8. customis triturated with diethyl ether and suction
  9. filtrationfiltered

Sources & evidence

ORD record
ord-9a5684583c124713b8f3efa1dcca2a5f
Source dataset
uspto-grants-2012_12
Patent number
US08334378B2

Reaction notes

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