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Product Details of [ 29274-24-6 ]

CAS No. :29274-24-6 MDL No. :MFCD04035683
Formula : C6H4ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :WEPRLWNMBTYGGD-UHFFFAOYSA-N
M.W : 153.57 Pubchem ID :21071759
Synonyms :

Calculated chemistry of [ 29274-24-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.0
TPSA : 30.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.29
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.823 mg/ml ; 0.00536 mol/l
Class : Soluble
Log S (Ali) : -1.52
Solubility : 4.6 mg/ml ; 0.0299 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.747 mg/ml ; 0.00486 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 29274-24-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29274-24-6 ]

* 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 [ 29274-24-6 ]
  • Downstream synthetic route of [ 29274-24-6 ]

[ 29274-24-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 29274-22-4 ]
  • [ 29274-24-6 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: for 3 h; Reflux
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
A mixture of pyrazolo[l ,5-a]pyrimidin-5-ol (17.0 g, 126 mmol) inPOCI3 (100 mL) was heated at reflux for 3 hours. After cooling, the reaction was concentrated under vacuum. To the residue was added dichloromethane. The organic phase was carefully washed with saturated aqueous NaHC03 solution, dried and concentrated. The crude product was purified by passing through a short silica gel pad eluting with 50percent> EtOAc in hexane to give 5-chloropyrazolo[l ,5-a]pyrimidine (13.1 g, 68percent>).
38% for 3 h; Reflux A mixture of pyrazolo[1,5-a]pyrimidin-5-ol (32.0 g, 237 mmol) and POCl3 (177 mL, 1.89 mol) was refluxed for 3 hours.
After being cooled to room temperature, the reaction mixture was concentrated in vacuo.
The residue was diluted with DCM, washed with saturated aq. NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo.
The residue was purified by column chromatography on SiO2 (DCM:MeOH=20:1) to afford 5-chloropyrazolo[1,5-a]pyrimidine (14.1 g, 38percent) as a yellow solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): δ 6.73 (1H, dd, J=2.0, 0.8 Hz), 7.14 (1H, d, J=7.2 Hz), 8.29 (1H, d, J=2.4 Hz), 9.19 (1H, dd, J=7.2, 0.8 Hz).
183.6 mg With trichlorophosphate In acetonitrile at 80℃; To a solution of 6-(difluoromethyl)-2-methylpy-rimidin-4(1H)-one (1.62 g) obtained in Step A of Reference Example 20 in acetonitrile (20 mE) was added phosphoryl chloride (2.83 mE), and the mixture was stirred overnight at 80° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel colunm chromatography (hexane/ethyl acetate) to give the title compound (866 mg). MS: [M+H]+179.0. The title compound (183.6 mg) was obtained using pyrazolo[1 ,5-a]pyrimidin-5-ol obtained in Step A of Reference Example 24 in the same manner as in Step B of Reference Example 20. MS: [M+H]+154.0.
Reference: [1] Patent: WO2011/29027, 2011, A1, . Location in patent: Page/Page column 42
[2] Patent: US2016/168156, 2016, A1, . Location in patent: Paragraph 0350; 0354; 0355
[3] Patent: WO2013/12915, 2013, A1, . Location in patent: Paragraph 00681
[4] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[5] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 351
[6] Patent: US2018/155333, 2018, A1, . Location in patent: Paragraph 1805; 1808; 1809; 1819; 1822; 1823
[7] Patent: WO2004/43940, 2004, A1, . Location in patent: Page 86
  • 2
  • [ 29274-22-4 ]
  • [ 29274-24-6 ]
YieldReaction ConditionsOperation in experiment
53% at 120℃; for 2 h; Inert atmosphere A solution of 4H-pyrazolo[1,5-a]pyrimidin-5-one (1 g, 7.40 mmol, 1 .00 equiv) in phosphorus oxychloride ( 1 5 mL) was stirred under nitrogen for 2 h at 1 20 °C. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a si lica gel column eluted with ethyl acetate/petroleum ether ( 1 :2) to give 0.6 g (53percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT = 1.21 min, m z = 154.0 [Μ+Η]
53% at 120℃; for 2 h; Inert atmosphere A solution of 4H-pyrazolo[1,5- a]pyrimidin-5-one (1 g, 7.40 mmol, 1 .00 equiv) in phosphorus oxychloride ( 1 5 mL) was stirred under nitrogen for 2 h at 1 20 °C. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a si lica gel column eluted with ethyl acetate/petroleum ether ( 1 :2) to give 0.6 g (53percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT = 1.21 min, m z = 154.0 [Μ+Η]
53% at 120℃; for 2 h; Inert atmosphere A solution of 4H-pyrazolo[1,5-a]pyrimidin-5-one (1 g, 7.40 mmol, 1 .00 equiv) in phosphorus oxychloride ( 1 5 mL) was stirred under nitrogen for 2 h at 1 20 °C. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a si lica gel column eluted with ethyl acetate/petroleum ether ( 1 :2) to give 0.6 g (53percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT = 1.21 min, m z = 154.0 [Μ+Η]
53% at 120℃; for 2 h; Inert atmosphere [0210] Step 2. 5-Chloro-pyrazolo [1,5-al pyrimidine. A solution of 4H-pyrazolo [1,5- a]pyrimidin-5-one (1 g, 7.40 mmol, 1.00 equiv) in phosphorus oxychloride (15 mL) was stirred under nitrogen for 2 h at 120 °C. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:2) to give 0.6 g (53percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT = 1.21 mi m/z = 154.0 [M+H].
1.52 g for 4 h; Reflux; Inert atmosphere 4H-pyrazolo [1,5-a] pyrimidin-5-one (1.35 g, 10 mmol)POCl3 (30 mL) was added,Heated to reflux,Reaction 4h,After completion of the reaction, the mixture was cooled to room temperature,concentrate,Redissolved in CH2Cl2,Followed by water, saturated NaHCO3,Washed with saturated brine, dried over anhydrous Na2SO4. Filter, concentrate,To give 5-chloropyrazolo [1,5-a] pyrimidine (1.52 g, yellow solid).
5.40 g at 110℃; for 3 h; A mixture of A-7 (10.00 g, 74.01 mmol) in POC13 (100 mL) wasstirred at 110 °C for 3 hours. The mixture was then concentrated, and the residue was diluted with a mixture of ice and H20 (200 mL), basified with NaHCO3 (solid) to pH—7-8, and extracted with EtOAc (150 mL x 2). The combined organic phase was washed with water (50 mL x 2)and brine (50 mL), dried over Na2504, filtered and concentrated to give the crude product, which was purified by silica gel (EtOAc in DCM = 1percent to 5percent) to afford A-7 (5.40 g, 34.97 mmol) as a solid. ‘H NMR (400 MHz, CDC13) on 8.59 (d, 1H), 8.14 (d, 1H), 6.82 (d, 1H), 6.64 (d, 1H). LCMS R = 0.537 mm in 1.5 mm chromatography, MS ESI calcd. for C6H5C1N3 [M+H1 154.0, found 153.8.

Reference: [1] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 142
[2] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 93; 94
[3] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 68
[4] Patent: WO2013/130935, 2013, A1, . Location in patent: Paragraph 0210
[5] Patent: WO2010/63487, 2010, A1, . Location in patent: Page/Page column 69
[6] Patent: CN104250252, 2017, B, . Location in patent: Paragraph 0095; 0099; 0100
[7] Patent: WO2018/98500, 2018, A1, . Location in patent: Page/Page column 84
  • 3
  • [ 1159981-95-9 ]
  • [ 29274-24-6 ]
Reference: [1] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 70
  • 4
  • [ 29274-24-6 ]
  • [ 960613-96-1 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 20℃; for 1 h;
Stage #2: With ammonia In water
Intermediate Example A Preparation of 3-bromo-5-chloro-pyrazolo[1 ,5- a]pyrimidine [Intermediate A]To a stirred solution of 5-Chloro-pyrazolo[1 ,5-a]pyrimidine (46.4 g, 0.3 mol), in glacial acetic acid (700 mL), at room temperature, was added bromine (42 mL, 0.81 mol) dropwise. On completion of addition, the mixture was stirred for 1 hour. The precipitate was filtered off, washed with glacial acetic acid and diethyl ether and dried. The filtrate was retained. The residue was suspended in water (500 mL) and the mixture neutralised with concentrated aqueous ammonia. The crude product was filtered, washed with water, isopropanol and hexane and dried to give 3-bromo-5-chloro-pyrazolo[1 ,5- a]pyrimidine [Intermediate A] (34.6 g, 49percent). The retained filtrate was diluted with ice water, neutralised with concentrated aqueous ammonia and the resulting crude product filtered, washed with isopropanol and hexane and dried to give further 3-bromo-5-chloro-pyrazolo[1 ,5-a]pyrimidine [Intermediate A] (23.6 g, 33percent). 1H-NMR (400 MHz, d6-DMSO): δ = 9.18 (2H, d), 8.41 (1 H, s), 7.19 (2H, d) ppm.
45% With N-Bromosuccinimide In dichloromethane at 20℃; for 1 h; To a solution of 5-chloropyrazolo[l,5-a]pyrimidine (2.30 g, 15.0 mmol) in dichloromethane (100 mL) was added N-bromosuccinimide (2.67 g, 15.0 mmol) and the mixture allowed to stir at ambient temperature for 1 hour. The reaction mixture was poured into water, extracted with dichloromethane, and dried over sodium sulfate. The crude product was purified by column chromatography, eluting with 1percent MeOH/dichloromethane and afforded 1.50 g (45percent) of 3-bromo-5-chloropyrazolo[l,5-a]pyrimidine as a light yellow solid.
39.8 g
Stage #1: at 20℃;
Stage #2: at 0℃; for 0.833333 h;
Part A. 3-Bromo-5-chloro-Dyrazoloil.5-alDyrimicline Sodium acetate [127-09-3] (24.1 g, 293.9 mmol) was added to a solution of 5-chloro- pyrazolo[l,5-a]pyrimidine [29274-24-6], (30.1 g, 195.7 mmol) in glacial acetic acid (395 mL) and allowed to stir at ambient temperature until all of the solid had dissolved. An ice bath was then put in place, and the solution chilled to 0°C. Bromine [7726-95-6] (11.0 mL, 214.7 mmol) was added drop by drop into the 0°C buffered acetic acid reaction solution over 35 minutes which gradually became a thick stirred suspension. Upon completion of the bromine addition, the suspension was allowed to stir for a further 15 minutes then was slowly poured into an aqueous (5percent w/v) solution (1 L) of sodium metabisulfite [7681-57-4] stirred in an ice bath. Solid sodium hydroxide [1310-73-2] pellets were added to the stirred suspension, at a rate to maintain an internal temperature of less than 40 °C, until pH of the supernatant was determined to be approximately 8 by pH paper. Precipitated product was isolated by filtration, the filter cake washed with water, and allowed to dry to afford 39.8 g of light yellow powder, mp. 173-174°C. *H NMR (400 MHz, DMSO-ds) δ ppm 7.22 (d, J=7.33 Hz, 1 H) 8.44 (s, 1 H) 9.21 (d, J=7.07 Hz, 1 H). NMR (100 MHz, DMSO-ds) δ ppm 82.84, 109.99, 138.94, 143.76, 145.61, 151.18. LRMS (ESI) m/z 231.8/233.8/235.8 [(M+H)]+, calc'd for CeHsBrCINs: 232.47.
44.2 g With N-Bromosuccinimide In acetonitrile at 20℃; for 1 h; To a mixture 5-chloropyrazolo[l,5- a]pyrimidine (30g, 195mmol) in acetonitrile (600 mL) was added N-bromosuccinimide (38.3g, 215mmol). The mixture was stirred at room temperature for 1 hour. Solid product was filtered off and washed with IN NaOH and water. Acetonitrile filtrate and all the washes was concentrated in vacuo and suspended in IN NaOH. The solid product was filtered and washed with water. This product was combined with previous solid and dried overnight to obtain 44.2g 3-bromo-5-chloro- pyrazolo[l,5-a]pyrimidine. LRMS (ESI) m/z 232/234 [(M+H)]+, calc'd for CeHsBrCINs: 232.47. LCMS (M+l, bromo pattern) = 233. *H NMR (400 MHz, CDC ) δ: 6.82 (d, 1H), 8.15 (broad S, 1H), 8.58 (d, 1H).
13.6 g With N-Bromosuccinimide In tetrahydrofuran at 5 - 20℃; for 1 h; Example 17
3-bromo-5-chloropyrazolo[1,5-a]pyrimidine
A solution of 5-chloropyrazolo[1,5-a]pyrimidine (9 g) in THF (147 mL) was stirred at 5°C.
The reaction mixture was added with N-bromosuccinimide (11 g) and stirred at room temperature for 1 hour.
The reaction mixture was added with a sodium hydrogen sulfite aqueous solution and stirred for 5 minutes followed by distillation of THF under reduced pressure.
The obtained residue was added with a saturated sodium carbonate aqueous solution and extracted with ethyl acetate.
The obtained organic layer was washed twice with a saturated sodium carbonate aqueous solution, once with water and once with a saturated sodium chloride aqueous solution.
The obtained organic layer was dried over sodium sulfate and filtered followed by distillation of the solvent to give the titled compound having the following physical characteristics (13.6 g).
TLC : Rf 0.40 (Hexane : Ethyl Acetate = 4 : 1);
1H-NMR (DMSO-d6) : δ 6.85 (d, 1H), 8.12 (s, 1H), 8.54 (d, 1H).

Reference: [1] Patent: WO2007/147647, 2007, A1, . Location in patent: Page/Page column 60
[2] Patent: WO2011/29027, 2011, A1, . Location in patent: Page/Page column 43
[3] Patent: WO2013/134228, 2013, A1, . Location in patent: Page/Page column 25
[4] Patent: WO2015/142714, 2015, A1, . Location in patent: Page/Page column 12
[5] Patent: EP2960234, 2015, A1, . Location in patent: Paragraph 0554
[6] Patent: WO2008/138889, 2008, A2, . Location in patent: Page/Page column 216
  • 5
  • [ 29274-24-6 ]
  • [ 923595-58-8 ]
YieldReaction ConditionsOperation in experiment
100% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (200 mg, 1.30 mmol) in DMF (2 mL) was added N-iodosuccinimide (322 mg, 1.86 mmol). The reaction was stirred at rt overnight, then diluted with EtOAc (100 mL), and washed with H2O (50 mL), saturated Na2S2O3 aqueous solution (50 mL) and brine (50 mL). The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as a pale yellow solid (390 mg, 100percent). [0309] MS (ESI, pos. ion) m/z: 279.9 [M+H]+. [0310] 1H NMR (400 MHz, CDCl3) δ (ppm): 8.57 (d, J=7.2 Hz, 1H), 8.16 (s, 1H), 6.86 (d, J=7.2 Hz, 1H)
96% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2 h; To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (1.00 g, 6.51 mmol) in DMF (13 mL) was added portionwise N-iodosuccinamide (1.61 g, 7.16 mmol) at room temperature.
The reaction mixture was stirred for 2 hours at room temperature.
After addition of water, the mixture was stirred for further 30 min at room temperature.
A precipitated solid was collected by filtration and dried under vacuum to afford 5-chloro-3-iodopyrazolo[1,5-a]pyrimidine (1.74 g, 96percent) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): δ 7.15 (1H, d, J=7.2 Hz), 8.34 (1H, s), 9.17 (1H, d, J=7.2 Hz).
89% With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 4 h; N-Iodosuccinimide (1.61 g, 7.16 mmol) was added to a solutionof 5-chloropyrazolo[1,5-a]pyrimidine (7) (1 g, 6.51 mmol) in anhydrousDMF (10 mL). After stirring at RT for 4 h the reaction was poured into 10percent sodium thiosulfate (75 mL). The resulting precipitate was isolated via filtration and dried (Whatman PS1 filterpaper) to give 19 as a pale brown solid (1.62 g, 89percent). 1H NMR δH (d6-DMSO, 300 MHz), 9.19 (d, J 7.2, 1H), 8.38 (s, 1H), 7.18 (d, J7.2, 1H). LC–MS tR 6.37 min; LC254 99percent; m/z 280.1/282.0 [M+H].This was used without further purification.
Reference: [1] Patent: US2014/234254, 2014, A1, . Location in patent: Paragraph 0308; 0309; 0310
[2] Patent: US2016/168156, 2016, A1, . Location in patent: Paragraph 0439; 0441; 0442
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6280 - 6296
[4] Patent: WO2007/13673, 2007, A1, . Location in patent: Page/Page column 31
  • 6
  • [ 29274-24-6 ]
  • [ 1224288-92-9 ]
Reference: [1] Patent: US2014/234254, 2014, A1,
  • 7
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 29274-24-6 ]
  • [ 1453176-67-4 ]
YieldReaction ConditionsOperation in experiment
52% at 100℃; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% at 100℃; Sealed tube A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% at 100℃; Sealed tube A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% at 100℃; [0211] Step 3. Pyrazolo[1,5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 °C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum.The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to yield 1.2 g (52percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 mi m/z = 178.0 [M+Hf’.
52% at 100℃; [0219] Step 3. PyrazolorL5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[l,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 °C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1.2 g (52percent) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 min, m/z = 178.0 [M+H]+.

Reference: [1] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 142
[2] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 93; 94
[3] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 68; 69
[4] Patent: WO2013/130935, 2013, A1, . Location in patent: Paragraph 0211
[5] Patent: WO2013/130943, 2013, A1, . Location in patent: Paragraph 0219
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