Dimethylamine → HCID 10298728, compound

HRID 396183Notes

Reaction equation

HRID 396183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[NH:5][C:6]1[C:15]2[CH:14]=[C:13]3[N:16]([C:20](=[O:30])[CH2:21][CH2:22][CH2:23]C(=O)CCCCl)[CH2:17][CH2:18][O:19][C:12]3=[CH:11][C:10]=2[N:9]=[CH:8][C:7]=1[C:31]#[N:32].[I-].[Na+].[CH3:39][NH:40][CH3:41].O1CCCC1.C(=O)(O)[O-].[Na+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[NH:5][C:6]1[C:15]2[CH:14]=[C:13]3[N:16]([C:20](=[O:30])[CH2:21][CH2:22][CH2:23][N:40]([CH3:41])[CH3:39])[CH2:17][CH2:18][O:19][C:12]3=[CH:11][C:10]=2[N:9]=[CH:8][C:7]=1[C:31]#[N:32]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 69958506HCID 69958506, compound

Product 1

HCID 10298728HCID 10298728, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

An amount of 500 mg (1.09 mmol) of 9-(3-chloro-4-fluoroanilino)-1-[4-(chlorobutyryl)butanoyl]-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile was stirred in N,N-dimethylformamide (4.5 mL), and to this was added sodium iodide (0.163 g, 1.69 mmol), tetrabutylammonium iodide (0.80 g, 0.22 mmol), and dimethylamine solution in tetrahydrofuran 2M (11 mL, 21.8 mmol). The mixture was heated at 45° C. for 4 hours and stirred at room temperature for an additional 16 hours. To this was added ethyl acetate and sodium bicarbonate solution, and after separation of the layers, the organic phase was dried over sodium sulfate and evaporated to obtain the crude product. Purification of the crude product was carried out by flash chromatography (20% acetone in methanol), to give a tan solid (129 mg, 33% yield), m.p. 165° C.; 1H NMR (DMSO-d6) δ 9.78 (bs, 1H), 8.69 (bs, 1H), 8.39 (s, 1H), 7.39 (m, 2H), 7.26 (s, 1H), 7.21 (m, 1H), 4.39 (t, 2H), 3.98 (t, 2H), 2.64 (t, 2H), 2.20 (t, 2H), 2.07 (s, 6H), 1.71 (m, 2H); HRMS (EI) m/z 467.1514 (M+1). Analysis for C24H23ClFN5O2.0.3H2O.0.3C2H5CO2CH3: Found: C, 60.22; H, 5.16; N, 14.12. Calcd: C, 60.56; H, 5.24; N, 14.01.

Workup

  1. customafter separation of the layers
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customto obtain the crude product
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-c7d8720005554998b8421ce6b70ce948
Source dataset
uspto-grants-2003_08
Patent number
US06608048B2

Reaction notes

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