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[ CAS No. 1276666-13-7 ] {[proInfo.proName]}

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Chemical Structure| 1276666-13-7
Chemical Structure| 1276666-13-7
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CAS No. :1276666-13-7 MDL No. :MFCD22665909
Formula : C13H16ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 265.74 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1276666-13-7 ]

* 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 [ 1276666-13-7 ]

[ 1276666-13-7 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 1276666-12-6 ]
  • [ 1276666-13-7 ]
YieldReaction ConditionsOperation in experiment
98.5% With sodium tetrahydroborate; sodium acetate; acetic acid In dichloromethane at 10℃; for 1h; 1; 2; 4; 6 Preparation of 5-chloro-2-(5-methyl-[1,4]diazepan-1-yl)-benzoxazole (compound of formula I) Sodium borohydride (11.97 g, 316.78 mmol) was added to acetic acid (190.07 g, 3167.89 mmol) in multiple portions at less than 60 ° C, then 150 ml of dichloromethane was added, the temperature was lowered to 10 ° C, and sodium acetate (25.97) was added. g, 316.78 mmol), further added bis-methanesulfonate compound II (150 g, 316.78 mmol), stirred at 10 ° C for 1 h, with a concentration of 5 mol / L hydrogen the sodium oxide solution was adjusted to pH=10, the organic phase was separated, and the aqueous phase was extracted twice with 75 ml of dichloromethane. the organic phase was combined and washed with water to neutral, dried over anhydrous sodium sulfate and concentrated to give a solid 82.84 g, yield 98.50%, purity More than 99%.
93.66% With sodium tetrahydroborate; sodium acetate; acetic acid In dichloromethane at 0 - 10℃; for 1.5h; ((S)-4-(5-chlorobenzoxazol-2-yl)-7-methyl[1,4]diazepan-1-yl)(5-methyl-2-[1,2,3]triazol-2-yl-phenyl)methanone (compound C) NaBH4 (2.40 g, 63.35 mmol) was added into acetic acid (25.30 g, 422.38 mmol) and stirred for 10 min at room temperature. DCM (200 mL) and sodium acetate (3.46 g, 42.23 mmol) were then added and stirred at 0-10 °C for 10 min. Compound 7 (20.00 g, 42.23 mmol) was then added and the resulting mixture stirred for 1.5 h. HCl aq. (2 mol/L) (50 mL) was then added to quench the reaction and the pH of the solution was adjusted to 9 with NaOH aq. (5 mol/L). The organic phase was separated and the aqueous layer was extracted with DCM (2 * 100 mL). The organic extracts were combined and washed with water, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to obtain (rac)-8 (10.5 g, 93.66%). Dibenzoyl-L-tartaric acid (33.7 g, 94.13 mmol) was dissolved in THF (40 mL) and the solution cooled to 10 °C. Compound (rac)-8 (10 g, 37.66 mmol) (dissolved in DCM (10 mL)/THF (60 mL)) was added drop-wise to the solution and left to stirred for 5 h at 20 °C. The slurry was filtered and the solid washed with THF (3 * 10 mL) to give a white solid 10.50 g. The L-DBT salt 8 (10 g, 16.03 mmol), iPAc (80 mL) and MeOH (30 mL) were added to a 250 ml round bottomed flask. The slurry stirred for 20 h at room temperature and filtered to give a white solid 6.70 g. The L-DBT salt 8 (5.20 g) was treat with NaOH aq. (4 mol/L) in DCM to give (s)-8, 2.20 g. Compound 9 (1.83 g, 8.28 mmol) was dissolved in DCM (25 mL) and cooled to 0-10 °C. Then the solution of (s)-8 (2.00 g, 7.53 mmol) in DCM (20 mL) and Et3N (0.91 g, 9.01 mmol) were added drop-wise and the resulting mixture stirred for 1 h. The reaction mixture was poured into water (50 mL). The organic phase was separated and the aqueous layer was extracted with DCM (2 * 25 mL). The organic extracts were combined and washed with water, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to obtain the crude product which was purified by recrystallization from acetonitrile/water (1:1) to give a white solid. Yield: 82% (2.78 g).
With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 15 - 20℃;
Stage #1: 4-[(2-amino-ethyl)-(5-chlorobenzoxazol-2-yl)amino]butan-2-one-bis-methanesulfonic acid salt With sodium acetate; sodium tris(acetoxy)borohydride In dichloromethane; acetic acid at 20℃; for 1h; Industry scale; Stage #2: With hydrogenchloride In dichloromethane; water; acetic acid at 10℃; for 0.5h; Stage #3: With sodium hydroxide In dichloromethane; water; acetic acid at 20℃; 3 Bis-MSA adduct 12 (17.19 kg, 36.27 mol), sodium acetate (2.97 kg, 36.3 mol) and DCM (152 kg, 115 L) were charged to a vessel. The resulting slurry was cooled to 15 °C and acetic acid (26.8 kg, this was the amount required for dissolution of the salt) was added maintaining an internal temperature below 20 °C. The batch was cooled to 15 °C andNa(OAc)3BH (9.25 kg, 43.6 mol) was charged via a glove bag over 30 min maintaining an internal temperature below 20 °C. The resulting solution was aged for 30 min at 20 °C, HPLC analysis showed the reaction to be complete. The batch was then cooled to 10 °C, 2N HC1 (38.80 kg) was added and the resulting solution was aged for 30 min at 10 °C. The mixture was then adjusted to pH 9 using 5 N NaOH maintaining an internal temperature below 20 °C. Once at pH 9 the layers were allowed to separate and the organic lower layer was ran off into a clean drum. DCM (76.2 kg, 57.5 L) was then added to the aqueous phase, the layers were mixed, allowed to separate, then the lower layer was combined with the previous organics (this step was repeated but HPLC of the third DCM layer showed that this was unnecessary as it only contained 12.5 g of rac-11 by assay). The combined DCM fractions were then charged to a 160 liter vessel and distilled to approximately 20 L (~1 volume of DCM). THF (44 kg) was charged to the vessel and the resulting stream was discharged into a clean drum and stored in the cold room prior to the next step in the reaction sequence. The final solution was found to contain 9,4 kg of rac-14. This stream was sufficiently pure to be used directly in the subsequent resolution

  • 3
  • [ 1276666-10-4 ]
  • [ 1276666-13-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 5 - 60 °C 2: anhydrous Sodium acetate; sodium tris(acetoxy)borohydride; glacial acetic acid / dichloromethane / 15 - 20 °C
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 25 - 60 °C / Industry scale 2.1: anhydrous Sodium acetate; sodium tris(acetoxy)borohydride / dichloromethane; glacial acetic acid / 1 h / 20 °C / Industry scale 2.2: 0.5 h / 10 °C 2.3: 20 °C / pH 9
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 20 °C 2.1: 1,3,5-trichloro-2,4,6-triazine / methanol / 12 h / 20 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: methanesulfonic acid / tetrahydrofuran / 6 h / 5 - 68 °C 1.2: 12 h 2.1: anhydrous Sodium acetate; glacial acetic acid; sodium tetrahydridoborate / ethanol / 2 h / 10 - 15 °C

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