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[ CAS No. 7051-34-5 ] {[proInfo.proName]}

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Chemical Structure| 7051-34-5
Chemical Structure| 7051-34-5
Structure of 7051-34-5 * Storage: {[proInfo.prStorage]}
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Product Citations

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. , et al. DOI: PubMed ID:

Abstract: Interest in development of potent, selective inhibitors of the phosphatase from the receptor type protein tyrosine phosphatase PTPRD as antiaddiction agents is supported by human genetics, mouse models and studies of our lead compound PTPRD phosphatase inhibitor, 7-butoxy illudalic acid analog 1 (7-BIA). We now report structure-activity relationships for almost 70 7-BIA-related compounds and results that nominate a 7- cyclopentyl methoxy analog as a candidate for further development. While efforts to design 7-BIA analogs with substitutions for other parts failed to yield potent inhibitors of PTPRDs phosphatase, ten 7-position substituted analogs displayed greater potency at PTPRD than 7-BIA. Several were more selective for PTPRD vs the receptor type protein tyrosine phosphatases S, F and J or the nonreceptor type protein tyrosine phosphatase N1 (PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B), phosphatases at which 7-BIA displays activity. In silico studies aided design of novel analogs. A 7-position cyclopentyl methoxy substituted 7-BIA analog termed NHB1109 displayed 600-700 nM potencies in inhibiting PTPRD and PTPRS, improved selectivity vs PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B phosphatases, no substantial potency at other protein tyrosine phosphatases screened, no significant potency at any of the targets of clin.-useful drugs identified in EUROFINS screens and significant oral bioavailability. Oral doses up to 200 mg/kg were well tolerated by mice, though higher doses resulted in reduced weight and apparent ileus without clear organ histopathol. NHB1109 provides a good candidate to advance to in vivo studies in addiction paradigms and toward human use to reduce reward from addictive substances.

Keywords: Receptor type protein tyrosine phosphatase ; Cell adhesion molecule ; Addiction ; Drug reward ; Opiates ; Stimulants

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 7051-34-5 ]

CAS No. :7051-34-5 MDL No. :MFCD00001306
Formula : C4H7Br Boiling Point : -
Linear Structure Formula :(C3H5)CH2Br InChI Key :AEILLAXRDHDKDY-UHFFFAOYSA-N
M.W : 135.00 Pubchem ID :81503
Synonyms :
Chemical Name :(Bromomethyl)cyclopropane

Calculated chemistry of [ 7051-34-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 27.1
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 2.03
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.69 mg/ml ; 0.0199 mol/l
Class : Very soluble
Log S (Ali) : -1.35
Solubility : 6.08 mg/ml ; 0.045 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.7
Solubility : 2.67 mg/ml ; 0.0198 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 7051-34-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7051-34-5 ]

* 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.

  • Upstream synthesis route of [ 7051-34-5 ]
  • Downstream synthetic route of [ 7051-34-5 ]

[ 7051-34-5 ] Synthesis Path-Upstream   1~47

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Reference: [1] Patent: US2004/48802, 2004, A1,
[2] Patent: US2009/274648, 2009, A1,
[3] Patent: US2009/304626, 2009, A1,
  • 2
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YieldReaction ConditionsOperation in experiment
77.5% With bromine; triphenylphosphine In <i>N</i>-methyl-acetamide Example 1
(for comparison)
1250 ml of dimethylformamide were placed into the reaction vessel, and then 280.8 g of triphenylphosphine and then 70 g of hydroxymethylcyclopropane were added, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere, and the solution was subsequently cooled to -10° C. Then, 158.3 g of bromine (that is to say 2 mol percent more than theoretically required) were metered in in the course of 4 hours.
The reaction mixture was worked up by distillation.
Bromomethylcyclopropane was obtained in a yield of 77.5percent of theory.
The purity of the product was over 97percent, the open-chain halogenoalkanes amounted to 0.6percent.
73% With triphenyl phosphite; bromine In N,N-dimethyl-formamide at -12 - 20℃; Inert atmosphere; Large scale 10062] Into a clean, dry reactor equipped with a stirrer and under nitrogen are successively loaded 4.63 kg of DMF (5.1 eqV) and then 4.53 kg of triphenylphosphite. 2.34 kg of bromine is then introduced while maintaining the temperature at less than 12° C. The stirring speed is regulated according to the fluidity of the reaction medium. When casting ends, a very thick medium with a yellow solid suspension is obtained.10063] The set point of the jacket is then adjusted to —12° C. and then 0.96 kg of cyclopropylmethanol is introduced in such a way as not to exceed a temperature of —5° C. On completion of the addition the whole is allowed to return slowly to room temperature. The set point of the jacket is then adjusted to 64° C. for distillation, which is carried out at a pressure of 13 mbar by collecting the first 24 to 30° C. fraction at the top of the colunm, then the second 30 to 40° C. fraction (partial reflux). Two fractions, Fl (1.38 kg) and F2 (293 g), are collected. The two fractions, after washing with carbonated water and then drying by means of CaC12, lead to a final product 2a (mass 1.316 kg) having a GC relative purity of 98.7percent with a yield of 73percent.
95 %Spectr. With 1-bromo-N,N,2-trimethyl-1-propen-1-amine In dichloromethane at 0 - 20℃; for 0.5 h; Inert atmosphere General procedure: Tetramethyl haloenamines 2a, 3 or 4 (1.1 equiv) were added at 0 °C to a solution of cyclopropyl carbinol in dry dichloromethane, then left at room temperature for 30 min. The cyclopropyl halides were quickly distilled under vacuum (bath temperature 60 °C) to avoid the formation of cyclobutyl and homoallylic halides. The halides were identical to authentic samples.
Reference: [1] Patent: US6008420, 1999, A,
[2] Patent: US2016/355452, 2016, A1, . Location in patent: Paragraph 0062; 0063
[3] Synthetic Communications, 1996, vol. 26, # 6, p. 1109 - 1115
[4] Journal of the Chemical Society, Chemical Communications, 1982, # 18, p. 1037 - 1039
[5] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573
[6] Chem. Zentralbl., 1911, vol. 82, # I, p. 66
[7] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 43[8] Chem. Zentralbl., 1914, vol. 85, # I, p. 1998
[9] Journal of the American Chemical Society, 1955, vol. 77, p. 6675
[10] Journal of the American Chemical Society, 1977, vol. 99, # 10, p. 3408 - 3414
[11] Justus Liebigs Annalen der Chemie, 1966, vol. 697, p. 100 - 110
[12] Canadian Journal of Chemistry, 1970, vol. 48, p. 3953 - 3957
[13] Justus Liebigs Annalen der Chemie, 1975, p. 2305 - 2317
[14] Journal of Organic Chemistry, 1979, vol. 44, p. 2842 - 2845
[15] Journal of Organic Chemistry, 1984, vol. 49, # 3, p. 431 - 435
[16] Canadian Journal of Chemistry, 1980, vol. 58, p. 1075 - 1079
[17] Patent: US4511566, 1985, A,
[18] Tetrahedron, 2016, vol. 72, # 3, p. 420 - 430
[19] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0036
  • 3
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YieldReaction ConditionsOperation in experiment
74% With hydrogen bromide In 1,4-dioxane; chloroform at 10 - 20℃; for 2 h; A stirrer and a thermometer were attached to a 30 mL three-necked flask, and 0.36 g (5.0 mmol) of (hydroxymethyl) cyclopropane and 5 mL of chloroform were added, followed by cooling to 10 ° C. with stirring. Next, 2.77 g (6.5 mmol) of 19percent hydrogen bromide / 1,4-dioxane solution was added dropwise, and then the reaction solution was heated to room temperature and stirring was continued for 2 hours. GC analysis was carried out on the obtained reaction solution, whereby the target compound (bromomethyl) cyclopropane was obtained in a yield of 74percent. In this reaction, bromocyclobutane as an isomer was produced in a yield of 9percent, and 4-bromo-1-butene was produced in a yield of 2percent, respectively.
Reference: [1] Patent: JP2017/14124, 2017, A, . Location in patent: Paragraph 0033
[2] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573
[3] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0036-0038; 0042-0052
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Reference: [1] Patent: US5973216, 1999, A,
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Reference: [1] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0039-0041
  • 6
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Reference: [1] Justus Liebigs Annalen der Chemie, 1925, vol. 445, p. 213
[2] Journal of the American Chemical Society, 1928, vol. 50, p. 1985
  • 7
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 5, p. 1592 - 1600
  • 8
  • [ 42392-28-9 ]
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Reference: [1] Synthetic Communications, 1990, vol. 20, # 7, p. 1011 - 1021
  • 9
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Reference: [1] Patent: US4141897, 1979, A,
  • 10
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Reference: [1] Journal of Organometallic Chemistry, 1974, vol. 73, p. 237 - 250
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1975, vol. 45, p. 1762 - 1767[2] Zhurnal Obshchei Khimii, 1975, vol. 45, # 8, p. 1796 - 1802
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 1, p. 119 - 122[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 1, p. 135 - 138
  • 13
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Reference: [1] Journal of Organometallic Chemistry, 1987, vol. 326, p. 281 - 288
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Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 10, p. 3221 - 3225
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
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Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 10, p. 3221 - 3225
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
  • 18
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Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 11 - 16
  • 19
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
  • 20
  • [ 506-68-3 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1925, vol. 445, p. 213
  • 21
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Reference: [1] Justus Liebigs Annalen der Chemie, 1925, vol. 445, p. 213
  • 22
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Reference: [1] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0039-0041
  • 23
  • [ 5911-08-0 ]
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 5, p. 1592 - 1600
  • 24
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 18, p. 6494 - 6505
  • 25
  • [ 186581-53-3 ]
  • [ 106-95-6 ]
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 1, p. 119 - 122[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 1, p. 135 - 138
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  • [ 1194-33-8 ]
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Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 10, p. 3221 - 3225
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
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Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 10, p. 3221 - 3225
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
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Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 11 - 16
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
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YieldReaction ConditionsOperation in experiment
62% With sodium carbonate In acetonitrile at 85℃; for 16 h; Example 192; f 5- 1-Cyclopropylmettlyl-piperidin-4-yloxy)-lH-indol-2-yll-morpholin-4-yl-methanone; a) Step 1: 1-Cyclopropylmethyl-piperidin-4-one; To a suspension of (bromomethyl)cyclopropane (500 mg, 4 mmol, 1.0 eq. ) and 4- piperidone hydrate hydrochloride (579 mg, 4 mmol, 1.0 eq. ) in acetonitrile (30 mL) was added sodium carbonate (1.148 g, 11 mmol, 3. eq. ). The reaction mixture was stirred 16 h at 85 °C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97: 3 to yield 339 mg (62 percent) of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100percent).
56% With sodium carbonate In water; acetonitrile at 85℃; Preparation 18: r-Cyclopropylmethyl-l,4'-bipiperidin-4-amine hydrochloride; [0130] A round bottom flask was charged with piperidin-4-one hydrochloride monohydrate (10 g, 65.1 mmol), acetonitrile (70 mL), bromomethylcyclopropane (8.79 g, 65.1 mmol), and sodium carbonate (20.7 g, 195.3 mmol). This mixture was heated overnight at 850C, then cooled, filtered and the filtrate concentrated. The product was purified by flash chromatography (16O g column, 0-7percent 2N NH3 in MeOH : DCM) to give l-(cyclopropylmethyl)piperidin-4-one as a yellow liquid (5.6 g, 56 percent yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.09 - 0.17 (m, 2 H) 0.52 - 0.59 (m, 2 H) 0.85 - 0.97 (m, 1 H) 2.38 (d, J=6.57 Hz, 2 H) 2.49 (t, J=6.19 Hz, 4 H) 2.84 (t, J=6.19 Hz, 4 H). MS (ES) [M+H] calculated for C30H37N9O2, 556; found 556. MS (ES) [M+H] calculated for C9Hi5NO, 154; found 154.[0131] To a solution of l-(cyclopropylmethyl)piperidin-4-one (750 mg, 4.9 mmol) and A- (BOC amino)piperidine (982 mg, 4.9 mmol) in THF (30 mL) was added AcOH (20 drops) and sodium triacetoxyborohydride (3.1 g, 14.7 mmol). This solution was allowed to stir overnight. Water (40 mL) was then added to the reaction, the layers separated, and the organic discarded. The aqueous layer was basified with sodium carbonate (10 mL sat.) and the product extracted into EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated to give tert-bvXy\\ r-(cyclopropylmethyl)-l,4'-bipiperidin-4- ylcarbamate (513 mg, 31 percent yield). MS (ES) [M+H] calculated for Ci9H35N3O2, 338; found 338. tert-Butyl r-(cyclopropylmethyl)-l,4'-bipiperidin-4-ylcarbamate (513 mg, 1.52 mmol) was dissolved in MeOH (15 mL), HCl was added (2 mL cone.) and the mixture was heated to 70 0C for 3 hours. The mixture was then cooled and the product was filtered off, washed with diethyl ether, and dried to yield the title compound (530 mg, quant, yield) as a white solid. MS (ES) [M+H] found 238.
Reference: [1] Patent: WO2005/123716, 2005, A1, . Location in patent: Page/Page column 94-95
[2] Patent: WO2010/25073, 2010, A1, . Location in patent: Page/Page column 29-30
[3] Patent: US2006/160855, 2006, A1, . Location in patent: Page/Page column 14
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Reference: [1] Patent: US2012/46247, 2012, A1, . Location in patent: Page/Page column 18-19
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Reference: [1] Tetrahedron, 2003, vol. 59, # 36, p. 7215 - 7229
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YieldReaction ConditionsOperation in experiment
74% With hydrogen bromide In 1,4-dioxane; chloroform at 10 - 20℃; for 2 h; A stirrer and a thermometer were attached to a 30 mL three-necked flask, and 0.36 g (5.0 mmol) of (hydroxymethyl) cyclopropane and 5 mL of chloroform were added, followed by cooling to 10 ° C. with stirring. Next, 2.77 g (6.5 mmol) of 19percent hydrogen bromide / 1,4-dioxane solution was added dropwise, and then the reaction solution was heated to room temperature and stirring was continued for 2 hours. GC analysis was carried out on the obtained reaction solution, whereby the target compound (bromomethyl) cyclopropane was obtained in a yield of 74percent. In this reaction, bromocyclobutane as an isomer was produced in a yield of 9percent, and 4-bromo-1-butene was produced in a yield of 2percent, respectively.
Reference: [1] Patent: JP2017/14124, 2017, A, . Location in patent: Paragraph 0033
[2] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573
[3] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0036-0038; 0042-0052
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Reference: [1] Patent: JP5979791, 2016, B2, . Location in patent: Paragraph 0039-0041
  • 37
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 5, p. 1592 - 1600
  • 38
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Reference: [1] Synthetic Communications, 1990, vol. 20, # 7, p. 1011 - 1021
  • 39
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 18, p. 6494 - 6505
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  • [ 4399-47-7 ]
  • [ 7051-34-5 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
  • 41
  • [ 75-09-2 ]
  • [ 2516-33-8 ]
  • [ 7789-60-8 ]
  • [ 5162-44-7 ]
  • [ 4399-47-7 ]
  • [ 7051-34-5 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2509,2515
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 74,77
  • 42
  • [ 157-33-5 ]
  • [ 5162-44-7 ]
  • [ 4399-47-7 ]
  • [ 7051-34-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 961 - 964[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1080 - 1083
  • 43
  • [ 594-61-6 ]
  • [ 7051-34-5 ]
  • [ 19444-23-6 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 5 - 20℃; for 1 h;
Stage #2: With potassium iodide In N,N-dimethyl-formamide at 100℃; for 3 h; Microwave irradiation
To a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60percent dispersion in mineral oil, 192 mg, 4.80 mmol) was added portionwise at 5°C. The resulting mixture was stirred lh at RT. The solvent was removed, the residue was suspended in dry DMF (7 ml) and (bromomethyl)benzene (821 mg, 4.80 mmol) was added followed by a catalytic amount of KI. The reaction was heated under microwave irradiation at 100°C for 3h. After cooling the solvent was evaporated and the residue was partitioned between water and EtOAc; the organic phase was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (EtO Ac/petroleum ether = 1/1) affording benzyl 2-hydroxy-2- methylpropanoate as a yellow liquid (773 mg, 3.98 mmol, 83percent yield).
Reference: [1] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 266
  • 44
  • [ 7051-34-5 ]
  • [ 603-35-0 ]
  • [ 14799-82-7 ]
YieldReaction ConditionsOperation in experiment
34 g at 100 - 110℃; for 6 h; 20 g (0.148 mol) of cyclopropylmethyl bromide, 39.3 g (0.15 mol) of triphenylphosphine and 30 ml of DMF were simultaneously charged into a 250 ml three-necked flask and the temperature was maintained at 100 to 110 ° C. for 6 hours The temperature was lowered to 50 ° C., After placing in 200 ml of ethyl acetate and stirring, a large amount of white solid appeared and was filtered to give 34 g of the product cyclopropylmethyltriphenylphosphine salt (2-a) as cyclopropyl bromide methyl bromide
Reference: [1] Chemical Communications, 2017, vol. 53, # 24, p. 3497 - 3500
[2] Chemical Communications, 2017, vol. 53, # 47, p. 6327 - 6330
[3] Journal of the American Chemical Society, 2009, vol. 131, # 36, p. 12918 - 12920
[4] Liebigs Annalen der Chemie, 1993, # 3, p. 231 - 236
[5] Journal of Organic Chemistry, 1993, vol. 58, # 2, p. 438 - 443
[6] Journal of Organic Chemistry, 1968, vol. 33, # 8, p. 3082 - 3088
[7] Justus Liebigs Annalen der Chemie, 1970, vol. 732, p. 151 - 164
[8] Angewandte Chemie, 1967, vol. 79, # 12, p. 576 - 577
[9] Patent: WO2007/29587, 2007, A1, . Location in patent: Page/Page column 47-48
[10] Patent: JP2016/113440, 2016, A, . Location in patent: Paragraph 0066
  • 45
  • [ 7051-34-5 ]
  • [ 151103-08-1 ]
  • [ 151103-09-2 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With potassium carbonate; potassium iodide In dimethyl sulfoxide at 70℃; for 1 h;
Stage #2: at 70℃; for 4 h;
55 g of 4-(difluoromethoxy)-3-hydroxybenzaldehyde, 42.42 g of K2C03 (1.05 eq), 4.86 g of Kl (0.1 eq) and 220 mL of dimethylsulphoxide (DMSO) were loaded in a reactor. The mixture was heated at 70°C and kept for 1 h. A mixture previously prepared of 42.65 g of bromomethyl cyclopropane (1.08 eq) and 1 10 mL of DMSO was added for 1 hour. The reaction was kept for 3 h at 70°C, and then cooled at room temperature. Once the temperature was reached, 375 mL of toluene was added. The suspension was filtered to remove the remaining K2C03, and then it was cooled at 0-5°C, and 375 mL of deionised water were loaded. The phases were separated and the organic phase was washed twice with 55 mL of deionised water. The solvent was removed at reduced pressure, obtaining 70 g (yield 99percent) of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)- benzaldehyde as a viscous yellowish fluid.
98.5% With trimethylbenzylammonium bromide; potassium carbonate; potassium iodide In tetrahydrofuran at 0℃; Reflux The 50g (266mmol) 4- difluoromethoxy-3-hydroxybenzaldehyde was dissolved was added potassium carbonate 91.9g (665mmol) in tetrahydrofuran 500mL, potassium iodide was added 2.2g (13.3mmol) and benzyl trimethyl ammonium bromide 3.7g, was added and cooled to 0 bromomethyl cyclopropane 50.6g (375mmol) in tetrahydrofuran (150 mL) solution, stirring the reaction mixture was heated to reflux for 1-3 hours, suction filtered, the filtrate was concentrated under reduced pressure, the residue was was added 2mol / L sodium hydroxide solution to pH10, extracted twice with 500mL of dichloromethane, the solvent of the organic layers were dried over sodium sulfate and removed under reduced pressure to give 3-cyclopropyl-methoxy-4-difluoromethoxy methoxybenzaldehyde 63.5g (261mmol), a yield of 98.5percent.
97% With potassium carbonate In tetrahydrofuran at 0℃; for 14 h; Heating / reflux 4-Difluoromethoxy-3-hydroxybenzaldehyde (10 g, 52.8 mmol) was dissolved in tetrahydrofuran (100 ml) added with potassium carbonate (44 g, 105 mmol), cooled to 0° C. and added with a solution of bromomethylcyclopropane (11 ml, 116.6 mmol) in tetrahydrofuran (50 ml).
The reaction mixture was heated to reflux under stirring for 7 hrs, then fresh bromomethylcyclopropane (5.5 ml, 58.3 mmol) was added and the heating continued for further 7 hrs.
The solvent was removed by vacuum distillation, then the mixture was added with 2 N sodium hydroxide (100 ml) and extracted with dichloromethane (2*100 ml).
The combined organic layers were dried over sodium sulphate (5 g) and the solvent removed under reduced pressure to afford 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (12 g, 50 mmol, 97percent yield), that was used without further purification.
96% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20 h; a)
3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde

4.70 g (24.98 mmol) 4-difluoromethoxy-3-hydroxybenzaldehyde are placed in 50 ml of dimethylformamide, 4.00 g (29.63 mmol) bromomethylcyclopropane and 3.50 g (25.32 mmol) potassium carbonate are added.
The reaction mixture is heated to 100° C. for 20 hours, then the dimethylformamide is concentrated by evaporation.
The residue is extracted with ethyl acetate and water, the organic phase is dried and evaporated to dryness.
Yield: 5.83 g (96percent of theoretical)
87.7% With 4-methyl-morpholine; zinc(II) nitrate In water; acetonitrile at 55℃; 2) Step 1) 3-hydroxy-4-fluoro-methoxybenzaldehyde (37.6g, 200mmol), bromomethyl cyclopropane(29.7g, 220mmol) and N- methylmorpholine (28.3g, 280mmol) and zinc nitrate (22.7g, 120mol)Carried out in acetonitrile mixed reaction, the reaction temperature of the mixture was 55 , after the reaction,The reaction solution was added water,Extracted with dichloromethane, concentrated, and recrystallized from methanol to give 3-cyclopropylmethoxy-4-difluoromethoxy benzaldehyde 42.5g, yield 87.7percent, purity 99.41percent.
82% With potassium carbonate In DMF (N,N-dimethyl-formamide) Step 1: Prepared as described for intermediate 1, using 3-hydroxy-4-25 difluoromethoxy-benzaldehyde (5 g, 26.89 mmol), anhydrous potassium carbonate (7.4 g, 53.62 mmol) and bromomethyl cyclopropane (4.5 g, 33.3 mmol) in dry DMF (50 ml). The reaction yielded 5.5 g (82 percent) of the product as viscous liquid which was used as such for step 2.
22.5 g With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24 h; To a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde (18.4 g, 98 mmol) in DMF (200 ml), potassium carbonate (29.7 g, 215 mmol) and KI (16.3 g, 98 mmol) were added followed by (bromomethyl)cyclopropane (14.28 ml, 148 mmol), and the resulting suspension was stirred at RT for 24 hours. The mixture was poured into water (800 ml) and extracted with diethyl ether (3×300 ml); the combined organic layers were dried over Na2SO4 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (22.5 g, 93 mmol, 94.8percent yield, MS/ESI+ 243.1 [MH]+). This product was used without purification.
22.5 g With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24 h; To a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde (18.4 g, 98 mmol) in DMF (200 ml), potassium carbonate (29.7 g, 215 mmol) and KI (16.3 g, 98 mmol) were added followed by (bromomethyl)cyclopropane (14.28 ml, 148 mmol) and the resulting suspension was stirred at RT for 24h. The mixture was poured into water (800 ml) and extracted with diethyl ether (3X300 ml); the combined organic layers were dried over Na2S04 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (22.5 g, 93 mmol, 94.8percent yield, MS/ESI+ 243.1 [MH] +). This product was used without purification.
31 g With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 2 h; Into the reaction flask added 3-hydroxy-4-difluoromethoxybenzaldehyde (21 g, 0.11 mol), cyclopropylmethyl bromide (18. 1 g, 0.13 mol), K2CO3 (18. 5 g) , then dissolved in 199. 5 g DMF and reacted at 85 ° C for 2 h with stirring. TLC monitoring until the reaction was complete. the reaction solution was filtrated , concentrated with CH2Cl2 , then for liquid extraction added CH2Cl2 , H2O into concentrated solution . The organic phase was dried and concentrated with anhydrous MgSO4 to give 31 g of a pale yellow 3-cyclopropylmethylenedioxy-4-(difluoromethoxy)benzaldehyde solution.

Reference: [1] Patent: WO2014/60464, 2014, A1, . Location in patent: Page/Page column 15
[2] Patent: CN105254559, 2016, A, . Location in patent: Paragraph 0041; 0042
[3] Patent: US2008/15226, 2008, A1, . Location in patent: Page/Page column 10
[4] Patent: US2006/116373, 2006, A1, . Location in patent: Page/Page column 6
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6900 - 6908
[6] Patent: CN105523922, 2016, A, . Location in patent: Paragraph 0023; 0032
[7] Patent: WO2004/22536, 2004, A1, . Location in patent: Page 36
[8] Patent: US5449686, 1995, A,
[9] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 0965
[10] Research on Chemical Intermediates, 2013, vol. 39, # 5, p. 2107 - 2113
[11] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 244
[12] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 793 - 816
[13] Patent: US2014/275551, 2014, A1, . Location in patent: Paragraph 0053
[14] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 22, p. 7332 - 7339
[15] Patent: CN106146296, 2016, A, . Location in patent: Paragraph 0018
[16] Patent: CN106883118, 2017, A, . Location in patent: Paragraph 0038; 0046-0048
[17] Patent: CN102964297, 2018, B, . Location in patent: Paragraph 0020-0021; 0277; 0279
  • 46
  • [ 7051-34-5 ]
  • [ 445305-93-1 ]
Reference: [1] Patent: US2004/48802, 2004, A1,
[2] Patent: US2009/274648, 2009, A1,
[3] Patent: US2009/304626, 2009, A1,
[4] Patent: US2007/99825, 2007, A1, . Location in patent: Page/Page column 35
  • 47
  • [ 269410-08-4 ]
  • [ 7051-34-5 ]
  • [ 1000801-75-1 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; N-N(Bromomethyl)cyclopropane (0.95 mg, 6.70 mmol, 0.70 mL, 95 percent) was added to a mixture of4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (1 .00 g, 5.15 mmol) and caesium carbonate (3.49 mg, 10.72 mmol) in dry N,N-dimethylformamide (20 mL) at 0°O. After stirring for 30 mm the ice-water bath was removed. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with brine (3x100 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to afforded 1.30 g (4.38 mmol, 85percent of theory) of the title compound. GO-MS (Method L9): R1 = 4.35 mm; mlz = 247 M1 H NMR (300 MHz, Ohloroform-d, Method M2) 6 7.81 (s, 1 H), 7.79 (s, 1 H), 3.99 (d, J = 7.1 Hz,2H), 1.32 (s, 12H), 1.27 (m, 1 H), 0.71 - 0.58 (m, 2H), 0.41 - 0.33 (m, 2H).
49%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333 h; Inert atmosphere
Stage #2: for 24 h; Inert atmosphere
To a reaction vessel containing sodium hydride (60 wtpercent dispersion in mineral oil)(3.09 g, 77.32 mmol) was added NN-dimethylformamide (30 mL) under a stream of nitrogen followed by 4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (10 g, 51.55 mmol) and the reaction mixture was stirred for 20 min at room temperature. Cyclopropylmethylbromide (8.7 g, 61.86 mmol) was then added and the reaction mixture was stirred for 24 h under an atmosphere of nitrogen. The reaction mixture was slowly poured over saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was then washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified via flash chromatography on silica gel (solvent gradient: 0percent-100percent EtOAc in cyclohexane) to afford 1- (cyclopropylmethyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (6.29 g, 49percent). LCMS (ESI): [M+H]+ = 249.2; lH NMR (400 MHz, CDC13) δ 7.80 (d, J= 7.4 Hz, 2H), 3.99 (d, J = 7.0 Hz, 2H), 1.32 (s, 12H), 1.29 - 1.26 (m, 1H), 0.69 - 0.60 (m, 2H), 0.41 - 0.33 (m, 2H).
48% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 14 h; To a stirred solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (8.00 g,41.2 mmol) in DMF (130 mL) was added potassium carbonate (17.1 g, 124 mmol) and(bromomethyl)cyclopropane (6.0 mL, 62 mmol). The mixture was stirred at 600 C for 14 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with half-saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silicagel chromatography gave 4.95 g (48 percent yield) of the titlecompound.LC-MS (Method 2): Rt = 1.12 mm; MS (ESIpos): mlz = 249 [M+H]1HNMR (400 MHz, DMSO-d6) O [ppm]: 0.314 (0.66), 0.318 (0.59), 0.325 (0.56), 0.330 (0.65),0.471 (0.53), 0.476 (0.61), 0.492 (0.62), 0.496 (0.57), 1.045 (0.78), 1.219 (1.70), 1.224 (16.00),3.295 (1.54), 3.927 (1.24), 3.946 (1.22), 7.542 (1.07), 7.544 (1.08), 7.932 (1.09).
48% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 14 h; To a stirred solution of 4-(4, 4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (purchased from Acros, CAS 269410-08-4, 8.00 g, 41 .2 mmol) in DMF (130 mL) was added potassium carbonate (17.1 g, 124 mmol) and (bromomethyl)cyclopropane (6.0 mL, 62 mmol). The mixture was stirred at 60° C for 14 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with half-saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silicagel chromatography gave 4.95 g (48 percent yield) of the title compound. LC-MS (Method 2): Rt = 1.12 min; MS (ESIpos): m/z = 249 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) _ [ppm]: 0.314 (0.66), 0.318 (0.59), 0.325 (0.56), 0.330 (0.65), 0.471 (0.53), 0.476 (0.61 ), 0.492 (0.62), 0.496 (0.57), 1.045 (0.78), 1 .219 (1 .70), 1 .224 (16.00), 3.295 (1.54), 3.927 (1.24), 3.946 (1.22), 7.542 (1 .07), 7.544 (1 .08), 7.932 (1.09).

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4196 - 4212
[2] Patent: WO2017/178416, 2017, A1, . Location in patent: Page/Page column 114; 115
[3] Patent: WO2014/210354, 2014, A1, . Location in patent: Page/Page column 47; 48
[4] Patent: WO2017/102091, 2017, A1, . Location in patent: Page/Page column 435
[5] Patent: WO2017/207534, 2017, A1, . Location in patent: Page/Page column 180
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 9080 - 9093
[7] Patent: WO2010/75270, 2010, A1, . Location in patent: Page/Page column 158
[8] Patent: WO2009/154557, 2009, A1, . Location in patent: Page/Page column 113-114
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