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[ CAS No. 338992-12-4 ] {[proInfo.proName]}

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Chemical Structure| 338992-12-4
Chemical Structure| 338992-12-4
Structure of 338992-12-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 338992-12-4 ]

CAS No. :338992-12-4 MDL No. :MFCD09955369
Formula : C21H22BrFN4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 461.33 Pubchem ID :-
Synonyms :

Safety of [ 338992-12-4 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 338992-12-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 338992-12-4 ]

[ 338992-12-4 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 50-00-0 ]
  • [ 338992-12-4 ]
  • [ 443913-73-3 ]
YieldReaction ConditionsOperation in experiment
85% With sodium triacetoxyborohydride; acetic acid; In methanol; dichloromethane; water; at 20℃; for 2h; 37% aqueous solution of formaldehyde (40 mg, 0.52 mmol) followed by NaBH(OAc)3 (120 mg, 0.56 mmol) were added in portions to the solution of 5a (167 mg, 0.4 mmol) and acetic acid (28 mg, 0.48 mmol) in CH2Cl2 (10 mL) and methanol (20 mL). After the reaction mixture was stirred at rt for 2 h, and the solvents were removed under vacuum. The resulting residue was added aqueous NaHCO3, the precipitate was filtered, washed with water and brine, and dried to obtainwhite solid; the aqueous layer was extracted with CH2Cl2, dried over MgSO4, filtered and evaporated to provide a residue, which was washed with Et2O to obtain white solid. The combined white solid gave 6a (146 mg, 85%).
45% A solution of N-(4-bromo-2-fluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amine (150 mg, 0.31 mmol, 1.00 equiv, 95%), formic acid (3 mL), and formaldehyde (3 mL, 85%) was was stirred at about 95 C. for about 4 hours and then concentrated in vacuo. After diluting the resulting residue with water (20 mL), the pH value was adjusted to 11 with 2M sodium hydroxide. The resulting solution was extracted with ethyl acetate (2*20 mL), washed with water (20 mL), washed with brine (20 mL), and then dried over anhydrous magnesium sulfate. The resulting residue was purified by silica gel column chromotography (dichloromethane/methanol 10:1) to give the title product as a white solid (70 mg, yield 45%). 1H NMR (300 MHz, DMSO) delta: 9.55 (s, 1H), 8.36 (s, 1H), 7.80 (s, 1H), 7.67 (dd, J=10.2, 2.1 Hz, 1H), 7.46-7.57 (m, 2H), 7.19 (s, 1H), 4.02 (d, J=5.7 Hz, 2H), 3.95 (s, 3H), 2.83-2.87 (m, 2H), 2.21 (s, 3H), 1.92-2.01 (m, 2H), 1.77-1.81 (m, 3H), 1.36-1.43 (m, 2H); LC-MS: m/z=475/477 (MH)+.
With sodium cyanoborohydride; In tetrahydrofuran; methanol; at 18 - 25℃; for 1h;Product distribution / selectivity; Example 2a A solution of 37% aqueous formaldehyde (50mul, 0.6mmol) followed by sodium cyanoborohydride (23mg, 0.36mmol) were added to a solution of 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (139mg, 0.3mmol), (prepared as described in Example 1), in a mixture of THF/methanol (1.4ml/1.4ml). After stirring for 1 hour at ambient temperature, water was added and the volatiles were removed under vacuum. The residue was triturated with water, filtered, washed with water, and dried under vacuum. The solid was purified by chromatography on neutral alumina eluding with methylene chloride followed by methylene chloride/ethyl acetate (1/1) followed by methylene chloride/ethyl acetate/methanol (50/45/5). The fractions containing the expected product were evaporated under vacuum. The resulting white solid was dissolved in methylene chloride/methanol (3ml/3ml) and 3N hydrogen chloride in ether (0.5ml) was added. The volatiles were removed under vacuum. The solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride (120mg, 69%). MS - ESI: 475-477 [MH]+
  • 3
  • [ 768350-54-5 ]
  • [ 338992-12-4 ]
  • 4
  • [ 92557-81-8 ]
  • [ 338992-12-4 ]
  • C42H32BrFN4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; Darkness;
  • 5
  • [ 64-18-6 ]
  • [ 338992-12-4 ]
  • [ 443913-73-3 ]
YieldReaction ConditionsOperation in experiment
84% With sodium tris(acetoxy)borohydride; acetic acid; In methanol; dichloromethane; at 20℃; for 2h; N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amine (30 mg, 0.065 mmol), sodium triacetoxyborohydride (19 mg, 0.091 mmol) was added to a flask containing formic acid (6 muL, 0.0845 mmol), acetic acid (5 muL, 0.078 mmol), DCM (1.6 mL) and methanol (3.2 mL). The flask was stirred for two hours at ambient temperature and then solvent removed under reduced pressure. Saturated NaHCO3 (3 mL) was added to the residue and the suspension filtered, washed with water (2 mL) and brine (2 mL). The filtrate was extracted with DCM (3 mL) and dried over MgSO4, solvent removed under reduced pressure, triturated with diethyl ether to afford the title compound as a white solid (6 mg, 84%). Mp: 226-228 C (lit 227-229 C 12); 1H NMR (500 MHz, d6-DMSO) delta: 1.44 (ddd, 2H, CH2, J = 3.9, 12.6, 24.8 Hz), 1.85 (d, 2H, CH2, J =12.5 Hz), 1.94-1.99 (m, 3H, CH and CH2), 2.32 (s, 3H, NCH3), 2.85 (d, 2H, CH2, J = 11.6 Hz), 3.98 (s, 3H, OCH3), 4.03 (d, 2H, OCH2, J = 5.5 Hz), 6.99 (s, 1H, ArH), 7.21 (s, 1H, ArH), 7.26 (s, 1H, ArH), 7.34 (d, 1H, ArH, J = 1.2 Hz), 7.36 (d, 1H, ArH, J = 1.2 Hz), 8.51 (s, 1H, ArH), 8.68 (brs, 1H, NH). 13C NMR (125 MHz, d6-DMSO) delta: 28.68, 34.92, 46.98, 49.32, 55.69, 70.65, 79.86, 102.82, 107.52 (d, J = 27.8), 108.91, 114.21, 114.74, 117.65, 121.21, 127.68, 131.32(d, J = 28.1 Hz), 153.04, 155.23, 155.99 (d, J = 132.3 Hz), 157.08, 158.86, 164.06. 19F NMR (471 MHz, d6-DMSO) delta: -115.86 (m, 1F). HRMS (ESI, m/z): calc?d for C21H25N4O2FBr [M+H]+ 462.1013 found: 462.1003
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