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[ CAS No. 7169-97-3 ] {[proInfo.proName]}

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Chemical Structure| 7169-97-3
Chemical Structure| 7169-97-3
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Product Details of [ 7169-97-3 ]

CAS No. :7169-97-3 MDL No. :MFCD00468968
Formula : C7H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :MJFCOXATGBYERZ-UHFFFAOYSA-N
M.W : 215.05 Pubchem ID :293097
Synonyms :

Calculated chemistry of [ 7169-97-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.25
TPSA : 41.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 1.05
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.68
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.68 mg/ml ; 0.00783 mol/l
Class : Soluble
Log S (Ali) : -1.52
Solubility : 6.46 mg/ml ; 0.03 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.27
Solubility : 0.115 mg/ml ; 0.000535 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 7169-97-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7169-97-3 ]

* 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.

  • Upstream synthesis route of [ 7169-97-3 ]
  • Downstream synthetic route of [ 7169-97-3 ]

[ 7169-97-3 ] Synthesis Path-Upstream   1~12

  • 1
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YieldReaction ConditionsOperation in experiment
99.04% at 20℃; Industrial scale To a 1 L four-necked flask equipped with a magnetic stirrer and thermometer, 46.04 g (0.267 mol) of 2-amino-5-Bromopyridine, was added 500mL dichloromethane at room temperature with stirring to dissolve slowly added dropwise 53.80g (0.527mol) acetic anhydride,Should be 2 to 5 hours, TLC control to the end of the reaction, vacuum distillation, the residue was dissolved in ethyl acetate, 200mL saturated sodium bicarbonateWashed twice and evaporated to dryness to give 56.41 g of 2-acetylamino-5-bromopyridine in a yield of 99.04percent.
92% With pyridine In tetrahydrofuran at 20℃; Step 63a: N-(5-bromopyridin-2-yl)acetamide (Compound 0601-112)To a solution of 2-amino-5-bromopyridine (0.50 g, 2.9 mmol) in THF (10 mL) was added pyridine (343 mg, 4.3 mmol) and acetic anhydride (295 mg, 2.9 mmol) at room temperature and stirred overnight. To the mixture water (30 mL) was added, extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated aqueous NaHC03 and brine, dried over Na2S04, concentrated to give the title compound (0.58 g, 92percent) as a white solid LCMS: 215 [M+2]+; 1HNMR (400 MHz, OMSO-d6) δ 2.09 (s, 3H), 7.97 (dd, J= 8.8, 2.4 Hz, 1H), 8.06 (d, J= 8.8 Hz, 1H), 8.41 (d, J= 1.2 Hz, 1H), 10.64 (s, 1H).
92% With pyridine In tetrahydrofuran at 20℃; Step 63a: N-(5-bromopyridin-2-yl)acetamide (Compound 0601-112)[0481]To a solution of 2-amino-5-bromopyridine (0.50 g, 2.9 mmol) in THF (10 mL) was added pyridine (343 mg, 4.3 mmol) and acetic anhydride (295 mg, 2.9 mmol) at room temperature and stirred overnight. To the mixture water (30 mL) was added, extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, concentrated to give the title compound (0.58 g, 92percent) as a white solid LCMS: 215 [M+2]+; 1HNMR (400 MHz, DMSO-d6) δ 2.09 (s, 3H), 7.97 (dd, J=8.8, 2.4 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H), 8.41 (d, J=1.2 Hz, 1H), 10.64 (s, 1H).
92% With pyridine In tetrahydrofuran at 20℃; Solution of pyridine (343mg, 4.3mmol) in THF (10mL) solution of 2-amino-5-bromopyridine (0.50g, 2.9mmol) and acetic anhydride (295mg, 2.9mmol) was stirred overnight then added at room temperature . With the addition of water (30mL) to the mixture, and the mixture was extracted with ethyl acetate (3x30mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, to afford the title compound as a white solid (0.58g, 92percent).
81% at 80℃; for 5 h; Synthesis of N-(5-bromopyridin-2-yl) acetamide [0293] A solution of 5-bromopyridin-2-amine (5.0 g, 28.90 mmol) in acetic anhydride (30 mL) was stirred at 80 °C for 5 h. After the consumption of the starting materials (monitored by TLC), the reaction was diluted with water (50 mL). The obtained solid was filtered and washed with hexane and dried in vacuo to afford N-(5-bromopyridin-2-yl) acetamide (5.0 g, 81percent) as a white solid. 1H-NMR (DMSO-<, 500 MHz): δ 10.61 ( s, 1H), 8.42 (s, 1H), 8.07 (d, 1H), 7.94 (d, 1H), 2.13 (s, 3H); LC-MS: 99.35percent; 217 (M+1); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 3.10 min. 5mM NH4OAc in water: ACN; 0.50 ml/min); TLC: 50percent EtOAc:hexane (R/. 0.3).
80% at 20℃; for 12 h; To a stirred solution of 5-Bromo-pyridin-2-ylamine (100 mg, 0.578 mmol) in dry THF was added acetic anhydride (70.25 mg, 0.693 mmol).
The reaction mixture was stirred at 20° C. for 12 hrs.
THF was distilled out and to it was added ethyl acetate.
The organic layer was washed with saturated NaHCO3 solution and dried over anhy sodium sulphate.
Removal of the solvent afforded N-(5-Bromo-pyridin-2-yl)-acetamide (100 mg, 80percent).
This was carried to next step without further purification.
75.4% at 100℃; for 9 h; A 2000 mL single-neck round bottom flask was charged with 2-amino-5-bromopyridine (86.50 g, 500 mmol)Acetic anhydride (153 g, 1500 mmol) and 850 ml of acetic acid,Start magnetic stirrer,The mixture in the reaction flask was stirred at 100 ° C for 9 hours.The TLC and GC tests confirmed that the starting 2-amino-5-bromopyridine was completely reacted,Water was added to the reaction solution,The reaction was then suction filtered, the filter cake was washed with ethyl acetate:N-hexane = 1: 4 to give the pure product 2-acetylamino-5-bromopyridine,The filtrate was extracted with ethyl acetate, the extract was removed by rotary evaporation,The crude product was obtained and recrystallized from ethyl acetate: n-hexane = 1: 4 to give the pure product2-acetamido-5-bromopyridine,After drying, the yield was calculated to be 75.40percent with a purity of 99.68percent (HPLC).

Reference: [1] Patent: CN103601745, 2017, B, . Location in patent: Paragraph 0029; 0030
[2] Tetrahedron Letters, 2002, vol. 43, # 17, p. 3121 - 3123
[3] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 205
[4] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0480; 0481
[5] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0414
[6] CrystEngComm, 2010, vol. 12, # 12, p. 4231 - 4239
[7] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 8, p. 875 - 880
[8] Patent: WO2015/66697, 2015, A1, . Location in patent: Paragraph 0293
[9] Patent: US2010/222325, 2010, A1, . Location in patent: Page/Page column 126
[10] Patent: CN106632016, 2017, A, . Location in patent: Paragraph 0013; 0014; 0015; 0016; 0017; 0018; 0019-0024
[11] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080
[12] Angewandte Chemie - International Edition, 2007, vol. 46, # 6, p. 930 - 933
[13] Patent: US6657063, 2003, B1, . Location in patent: Page column 92
[14] Patent: WO2006/79791, 2006, A1, . Location in patent: Page/Page column 42
[15] Patent: WO2009/145360, 2009, A1, . Location in patent: Page/Page column 68-69
[16] Patent: EP842924, 1998, A1,
  • 2
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YieldReaction ConditionsOperation in experiment
39% for 48 h; The 5-bromo-2-aminopyridine(5.8 mmol) and acetyl chloride (7.6 mmol) dissolved in 10 ml ofacetone, stirring 48 hours. After concentrating by get the crude product bycolumn chromatography (dichloromethane/methanol =250/1) title compoundseparated to obtain 480 mg (39percent). 1 H-NMR (CDCl 3) δ 9.08(1H, brs), 8.30 (2H, s), 7.92 (1H, m), 2.27 (3H, s).
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 25, p. 7050 - 7066
[2] Patent: US2003/166620, 2003, A1,
[3] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0204-0206
[4] Patent: WO2004/814, 2003, A1, . Location in patent: Page 84
  • 3
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YieldReaction ConditionsOperation in experiment
91% at 10 - 20℃; General procedure: Phosphoric acid (0.7 mL, 12 mmol) was added to acetonitrile (0.5 mL, 9.5 mmol), the resulting mixture was cooled to 10-15 °C. Then, a mixture of aminopyridine 1a-g (2 mmol) and sodium nitrite (0.56 g, 8 mmol) pretriturated in a mortar was added in small portions at such a rate that allowed us to avoid vigorous liberation of nitrogen oxides. The resulting paste was thoroughly triturated and allowed to stand at 10-15 °C for 10 min and then at 20 °C for the period of time indicated in Table 1. The reaction progress was monitored by TLC (eluent hexane-acetone, 1 : 3) and GCMS. Upon completion, the reaction mixture was diluted with water, neutralized with NaHCO3, and extracted with ethyl acetate. The organic layer was separated and dried with Na2SO4, the solvent was evaporated. Compounds 2a-g were purified by recrystallization from ethanol. Yields and m.p. of compounds 2a-g are summarized in Table 1. NMR spectra and m.p. of compounds obtained correspond to the data published for authentic samples.
Reference: [1] Russian Chemical Bulletin, 2016, vol. 65, # 9, p. 2312 - 2314[2] Izv. Akad. Nauk, Ser. Khim., 2016, # 9, p. 2312 - 2314,3
  • 4
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Reference: [1] Patent: US2002/173506, 2002, A1,
[2] Patent: US6001856, 1999, A,
[3] Patent: EP887079, 1998, A1,
[4] Patent: US6291489, 2001, B1,
  • 5
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Reference: [1] Synlett, 2008, # 17, p. 2579 - 2582
  • 6
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Reference: [1] New Journal of Chemistry, 2015, vol. 39, # 11, p. 8329 - 8336
  • 7
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Reference: [1] Patent: WO2007/124345, 2007, A2, . Location in patent: Page/Page column 24-25
  • 8
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Reference: [1] Patent: US2004/102450, 2004, A1, . Location in patent: Page/Page column 79
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1407 - 1412
  • 9
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Reference: [1] Synthesis, 2007, # 1, p. 81 - 84
  • 10
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 3, p. 666 - 674
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  • [ 1493-13-6 ]
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  • [ 475106-12-8 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 28, p. 3771 - 3773
  • 12
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  • [ 167837-43-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 21, p. 4053 - 4061
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