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[ CAS No. 24186-78-5 ] {[proInfo.proName]}

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Chemical Structure| 24186-78-5
Chemical Structure| 24186-78-5
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Product Details of [ 24186-78-5 ]

CAS No. :24186-78-5 MDL No. :MFCD16040307
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 167.16 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 24186-78-5 ]

* 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 [ 24186-78-5 ]

[ 24186-78-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 24186-78-5 ]
  • [ 250275-15-1 ]
  • [ 946488-67-1 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; EXAMPLE 31; 3,3-Difluoro-cyclobutanecarboxylic Acid ((S)-3-{5-[2,4-dimethyl-6-oxo-1-(2,2,2-trifluoro-ethyl)-1,6-dihydro-pyridine-3-carbonyl]-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl}-1-phenyl-propyl)-amide (III-23); step 1-; A solution of 68b (4.44 g), 2, (4.7 g), TEA (5.6 g), TBTU (9.25 g) in DCM and was stirred at RT overnight. The reaction mixture was poured into water and extracted with DCM, dried (Na2SO4), filtered and volatiles removed in vacuo. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (0-6% MeOH containing 0.5% NH4OH) to afford 5.73 g of 139.
  • 2
  • [ 64-17-5 ]
  • [ 24186-78-5 ]
  • [ 54453-94-0 ]
YieldReaction ConditionsOperation in experiment
74% A suspension of 2,4-dimethyl-6-oxo-l,6-dihydro-3-pyridinecarboxylic acid (890 mg, 5.32 mmol) in phosphorus oxychloride (8.9 mL, 95.19 mmol), was stirred at 80 C for 6 hrs. The reaction mixture was cooled to r.t. and then the solvent was evaporated. The residue was cooled to 0 C and EtOH (3.5 mL) was added dropwise. The mixture was stirred at r.t. for 30 min, then partitioned between EtOAc and H2O. The organic phase was concentrated in vacuo and the residue was taken up with phosphorus oxychloride (4 mL) and stirred for an additional 18 hrs at 80 C. The mixture was cooled to r.t. and then the solvent was evaporated. The residue was cooled to 0 C and EtOH (3 mL) was added dropwise. The mixture was stirred at r.t. for 1.5 hrs and then partitioned between EtOAc and H2O. The organic phase was concentrated under reduced pressure and the residue was purified by normal phase column chromatography on a 25 g silica gel column using a 0 to 20% gradient of EtOAc in cyclohexane as eluent. The title compound (842 mg, 3.94 mmol, 74% yield) was obtained as a colorless oil. NMR (400 MHz, DMSO-de) d 7.37 (s, 1H), 4.38 (q, J= 7.19 Hz, 2H), 2.43 (s, 3H), 2.30 (s, 3H), 1.33 (t, J= 7.15 Hz, 3H). MS-ESI (m/z) calc’d for C10H13CINO2 [M+H]+: 214.1, 216.1. Found 214.1, 216.1.
EXAMPLE 30; Tetrahydro-furan-3-carboxylic Acid [(S)-3-[5-(6-ethynyl-2,4-dimethyl-pyridine-3-carbonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-1-(3-fluoro-phenyl)-propyl]-amide (I-52); step 1-; A mixture of 68b (5.0 g, 29.91 mmol) was suspended in POCl3 (50 mL) and stirred at 85 C. degrees over night. The solvent was mostly evaporated. The residue was slowly poured into ice cold EtOH, stirred for 30 min and then partitioned between EtOAc and brine. The layers were separated and the aqueous layer was extracted EtOAc. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified via SiO2 chromatography which afforded 136a sufficiently pure to be used in the next step.
step 1 - A suspension of 80 (5g, 29.9 mmol) in 50 ml of POCI3 was stirred at 80 C overnight, cooled to RT and carefully evaporated. The residue was cooled to 0 C and EtOH (20 mL) was dropwise. The mixture was stirred at RT for 30 min then partitioned between EtOAc and H2O. The aqueous layer was back extracted with EtOAc. Combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 10% EtOAc) to afford 82a.
  • 3
  • [ 101251-72-3 ]
  • [ 24186-78-5 ]
  • [ 630082-81-4 ]
YieldReaction ConditionsOperation in experiment
1: 26% 2: 52% Stage #1: 6-chloro-2,4-dimethylnicotinonitrile With sulfuric acid In water at 120℃; for 16h; Stage #2: With sodium nitrite In water at 90℃; for 3h; 69.1; 60.1 Step 1: 6-Chloro-2,4-dimethylnicotinic acid 6-Chloro-2,4-dimethylnicotinonitrile (5.0 g, 30.01 mmol, 1 eq) was dissolved in a mixture of sulfuric acid (10.4 mL, 195.07 mmol, 6.5 eq) and water (9 mL). The mixture was heated at 120 °C for 16 hrs. Then it was then cooled to 90 °C and sodium nitrite (14.49 g, 210.07 mmol, 7 eq) was added in small portions over 10 minutes. The reaction was heated at 90 °C for an additional hour. Then other 3.5 eq. of NaNC were added portionwise and the mixture was stirred at 90 °C for additional 2 hrs. The mixture was cooled to r.t. and poured into an ice-water mix. The chilled mixture was basified to pH = 12 using NaOH aq. 10N. The aqueous mixture was then washed with DCM (2x) to remove impurities. The pH was then adjusted to 2 by adding HC1 aq. 6N and a mixture 4: 1 of DCM/MeOH was added. The off- white solid at the interphase was recovered by filtration and proved to be 6-hydroxy-2,4- dimethylpyridine-3 -carboxylic acid (1.3 g, 7.77 mmol, 26% yield). NMR (400 MHz, DMSO-de) d 12.90 - 11.00 (m, 2H), 6.05 (s, 1H), 2.30 (s, 3H), 2.18 (s, 3H). MS-ESI (m/z) calculated for CsHioNCb [M+H]+: 168.1. Found 168.2. The filtrate was also recovered, the 2 phases separated, the aqueous layer extracted with DCM/MeOH 4/1 (2x) and the combined extracts were washed with water, dried over anhydrous Na2S04 and concentrated to dryness to afford the title compound (2.9 g, 15.62 mmol, 52% yield). 'H NMR (400 MHz, DMSO-de) d 13.84 - 13.55 (bs, 1H), 7.34 (s, 1H), 2.45 (s, 3H), 2.31 (s, 3H). MS-ESI (m/z) calculated for C8H9CINO2 [M+H]+: 186.0. Found 186.2.
  • 4
  • [ 24186-78-5 ]
  • [ 64-17-5 ]
  • [ 54453-94-0 ]
YieldReaction ConditionsOperation in experiment
42.73% A suspension of 6-hydroxy-2,4-dimethylnicotinic acid (1.3 g, 7.78 mmol, 1 eq) in Phosphorus(V) oxychloride (13.09 mL, 139.99 mmol, 18 eq) was stirred at 100 C overnight. Then the mixture was cooled to room temperature and evaporated to dryness. The residue was cooled to 0 C and EtOH (7 mL) was added dropwise. The mixture was stirred at r.t. for 1.5 hrs, then partitioned between EtOAc and H2O. The organic phase was concentrated in vacuo and the residue was purified by normal phase chromatography on a 50 g silica gel column, using as eluent a gradient of EtOAc in cyclohexane, from 0 to 20% to afford the title compound (710 mg, 3.323 mmol, 42.73% yield) as a colorless oil. NMR (400MHz, CDCh) d 7.06 (s, 1H), 4.44 (q, J= 7.1 Hz, 2H), 2.55 (s, 3H), 2.34 (s, 3H), 1.42 (t, J= 7.2 Hz, 3H). MS-ESI (m/z) calc’d for C10H13CINO2 [M+H]+: 214.1. Found 214.2.
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