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[ CAS No. 89673-36-9 ]

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2D
Chemical Structure| 89673-36-9
Chemical Structure| 89673-36-9
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Quality Control of [ 89673-36-9 ]

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Related Doc. of [ 89673-36-9 ]

SDS

Product Details of [ 89673-36-9 ]

CAS No. :89673-36-9MDL No. :MFCD22056377
Formula :C13H15NO2SBoiling Point :333.4±15.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :249.33Pubchem ID :13182766
Synonyms :

Computed Properties of [ 89673-36-9 ]

TPSA : 66.6 H-Bond Acceptor Count : 3
XLogP3 : 3.8 H-Bond Donor Count : 1
SP3 : 0.31 Rotatable Bond Count : 3

Safety of [ 89673-36-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89673-36-9 ]

  • Upstream synthesis route of [ 89673-36-9 ]
  • Downstream synthetic route of [ 89673-36-9 ]

[ 89673-36-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 6314-28-9 ]
  • [ 75-65-0 ]
  • [ 89673-36-9 ]
YieldReaction ConditionsOperation in experiment
94% for 8.00 h; Heating / reflux Benzo[Z>]thiophen-2-yl-carbamic acid tert-butyl ester (1-B).; A solution of compound 1-A (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in -butanol (150 mL) was heated at reflux for 8 h. The solvent was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford compound 1-B as a colorless solid (18.9 g, 94percent). 1H-NMR (DMSO-^): δ 1.50 (s, 9H), <n="183"/>6.78 (s, IH), 7.16 (d of d, IH), 7.27 (d of d, IH), 7.58 (d, IH), 7.77 (d, IH), 10.70 (br s, IH); MS: m/z 250.2 (MH+).
94% for 8.00 h; Reflux B.
Benzo[b]thiophen-2-yl-carbamic acid tert-butyl ester (1d).
A solution of 2-carboxybenzo[b]thiophene (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in t-butanol (150 mL) was heated at reflux for 8 hours.
The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel, using dichloromethane as the eluant, to give the product as a colorless solid (18.9 g, 94percent).
1H NMR (DMSO-d6): δ 1.50 (s, 9H), 6.78 (s, 1H), 7.16 (d of d, 1H), 7.27 (d of d, 1H), 7.58 (d, 1H) and 7.77 (d, 1H), 10.70 (br s, 1H); MS: m/z 250.2 (MH+).
94% for 8.00 h; Reflux Example 1
benzo[b]thiophen-2-yl-carbamic acid tert-butyl ester (1-B).
A solution of compound 1-A (14.4 g, 80.6 mmol), N,N-diisopropylethylamine (15.5 mL, 88.6 mmol) and diphenylphosphoryl azide (20.8 mL, 96.7 mmol) in t-butanol (150 mL) was heated at reflux for 8 h.
The solvent was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with dichloromethane, to afford compound 1-B as a colorless solid (18.9 g, 94percent).
1H-NMR (DMSO-d6): δ 1.50 (s, 9H), 6.78 (s, 1H), 7.16 (d of d, 1H), 7.27 (d of d, 1H), 7.58 (d, 1H), 7.77 (d, 1H), 10.70 (br s, 1H); MS: m/z 250.2 (MH+).
64% for 5.00 h; Heating / reflux A solution of benzo[b]thiophene-2 carboxylic acid (1.25 g, 7.03 mmol), diphenylphosphoryl azide (1.94 g, 7.03 mmol) and triethylamine (0.98 mL, 7.03 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate and then concentrated to afford a beige solid. Purification by column chromatography (SiO2 DCM/Hexanes) afforded compound 235 as a white solid 0.96 g (64percent). HPLC-MS tR=2.7 Min(UV254 nm). Mass calculated for formula C13H15NO2S, M+249.33, observed LC/MS m/z 250.40 (M+H).
64% for 5.00 h; Heating / reflux Example 235; A solution of benzo[b]thiophene-2 carboxylic acid (1.25 g, 7.03 mmol), diphenylphosphoryl azide (1.94 g, 7.03 mmol) and triethylamine (0.98 mL, 7.03 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate and then concentrated to afford a beige solid. Purification by column chromatography (SiO2 DCM/Hexanes) afforded compound 235 as a white solid 0.96 g (64percent). HPLC-MS tR=2.7 Min (UV254nm). Mass calculated for formula C13H15NO2S, M+ 249.33, observed LC/MS m/z 250.40 (M+H).
62% for 16.00 h; Heating / reflux Example 36; Preparation of 3-(1 -benzothien-2-yl)-6-(3-fluoro-2-hvdroxyphenyl)-2-methyl-5-(2- phenylethyl)-4(3H)-pvrimidinone; [00115] a; 1 ,1-Dimethylethyl 1-benzothien-2-ylcarbamate; EPO <DP n="39"/>[00116] To a solution of i-benzothiophene-2-carboxylic acid (5.0 g, 0.028 mol) in dry NBuOH (70 ml_) was added TEA (4.3 ml_, 0.031 mol). After 5 min. of stirring, DPPA (6.67 ml_, 0.031 mol) was added and the reaction was refluxed for 16 h. The reaction was concentrated and the resulting residue was diluted with ethyl acetate and washed successively with sat. NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated before purifying by silica chromatography (0 - 40percent ethyl acetate/hexane) to afford pure product (4.35 g) in 62percent yield. 1H NMR (400 MHz, DMSO-Cf6) .pound. ppm 1.50 (s, 9 H), 6.77 (s, 1 H), 7.15 (t, J=0.85 Hz, 1 H), 7.26 (t, J=0.85 Hz, 1 H), 7.59 (d, J=7.79 Hz, 1 H), 7.76 (d, J=7.78 Hz, 1 H), 10.2 (brs, 1 H).

Reference: [1] Patent: WO2009/12430, 2009, A1. Location in patent: Page/Page column 180-181
[2] Patent: US2010/160289, 2010, A1. Location in patent: Page/Page column 24-25
[3] Patent: US2012/190674, 2012, A1. Location in patent: Page/Page column 73
[4] Patent: US2007/105864, 2007, A1. Location in patent: Page/Page column 193
[5] Patent: US2007/117804, 2007, A1. Location in patent: Page/Page column 125
[6] Patent: WO2006/41968, 2006, A1. Location in patent: Page/Page column 37-38
  • 2
  • [ 143944-01-8 ]
  • [ 89673-36-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
  • 3
  • [ 143944-01-8 ]
  • [ 98-86-2 ]
  • [ 89673-36-9 ]
  • [ 143944-02-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
  • 4
  • [ 89564-07-8 ]
  • [ 89673-36-9 ]
  • [ 143944-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
  • 5
  • [ 90490-31-6 ]
  • [ 89673-36-9 ]
  • [ 143944-02-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
  • 6
  • [ 39827-11-7 ]
  • [ 89673-36-9 ]
Reference: [1] Synthesis, 1983, # 11, p. 932 - 933
  • 7
  • [ 90490-31-6 ]
  • [ 98-86-2 ]
  • [ 89673-36-9 ]
  • [ 143944-02-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
[2] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 905 - 909
  • 8
  • [ 78140-97-3 ]
  • [ 75-65-0 ]
  • [ 89673-36-9 ]
  • [ 90490-39-4 ]
Reference: [1] Synthesis, 1983, # 11, p. 932 - 933
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