[ CAS No. 53525-65-8 ] {[proInfo.proName]}

Name: 53525-65-8|Diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione|95%
Brand: Ambeed
SKU: A159530
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Quality Control of [ 53525-65-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 53525-65-8 ]

CAS No. :	53525-65-8	MDL No. :	MFCD01631199
Formula :	C₈H₄N₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UYAAVKFHBMJOJZ-UHFFFAOYSA-N
M.W :	188.14	Pubchem ID :	1051510
Synonyms :

Calculated chemistry of [ 53525-65-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.67
TPSA :	68.74 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.64
Log Po/w (XLOGP3) :	-0.07
Log Po/w (WLOGP) :	-0.86
Log Po/w (MLOGP) :	-0.34
Log Po/w (SILICOS-IT) :	-0.26
Consensus Log Po/w :	-0.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.6
Solubility :	4.76 mg/ml ; 0.0253 mol/l
Class :	Very soluble
Log S (Ali) :	-0.92
Solubility :	22.5 mg/ml ; 0.12 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.58
Solubility :	4.91 mg/ml ; 0.0261 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 53525-65-8 ]

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

Application In Synthesis of [ 53525-65-8 ]

* 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 [ 53525-65-8 ]
Downstream synthetic route of [ 53525-65-8 ]

[ 53525-65-8 ] Synthesis Path-Upstream 1~6

1
[ 1072-84-0 ]
[ 53525-65-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	for 18 h; Reflux	The imidazole-2-carboxylic acid (5 g, 44.6 mmol) in suspensionin thionyl chloride (75 mL) was heated to reflux under agitation for18 h. The reaction mixture was cooled, then filtered, washed withtoluene, and dried under high vacuum. The compound is obtainedas a yellow solid (95percent yield). C8H4N4O2. MW: 188.14 g/mol. Mp265-268 °C. 1H NMR δ (ppm, 300 MHz, DMSO-d6) 8.24 (d, 1H,CHC-CO), 8.32 (d, 1H, CHC-CO, J3 Hz), 8.88 (d, 1H, CHN),9.28 (d, 1H, CHN, J3 Hz). 13C NMR δ (ppm, 100 MHz, DMSO-d6)123.99, 124.52, 125.62, 137.26, 139.73, 150.39, 159.68. MS (ESI+ ,QTof, m/z): 189.0 [M+H]+.

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 13, p. 6601 - 6610
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 909 - 919
[3] Pharmaceutical Chemistry Journal, 1986, vol. 20, # 7, p. 460 - 463[4] Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 7, p. 799 - 802
[5] Patent: EP1439169, 2004, A1, . Location in patent: Page 81-82

2
[ 1072-84-0 ]
[ 53525-65-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 457 - 460

3
[ 17325-26-7 ]
[ 53525-65-8 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 3, p. 306 - 309

4
[ 13189-13-4 ]
[ 53525-65-8 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 3, p. 306 - 309

5
[ 56460-32-3 ]
[ 53525-65-8 ]

Reference： [1] Tetrahedron Letters, 2001, vol. 42, # 26, p. 4297 - 4299

6
[ 61985-23-7 ]
[ 53525-65-8 ]
[ 79711-73-2 ]
[ 99560-60-8 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 3, p. 306 - 309

[ 53525-65-8 ] Synthesis Path-Downstream 1~36

1
[ 53525-65-8 ]
[ 23785-21-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 303 - 307

2
[ 53525-65-8 ]
[ 60-15-1 ]
[ 99240-58-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 460 - 463
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 799 - 802

3
[ 53525-65-8 ]
[ 124-40-3 ]
4⁽⁵⁾-(N,N-dimethylcarbamoyl)imidazole hydrobromide [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 460 - 463
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 799 - 802

4
[ 1072-84-0 ]
[ 53525-65-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With thionyl chloride; for 18h;Reflux;	The imidazole-2-carboxylic acid (5 g, 44.6 mmol) in suspensionin thionyl chloride (75 mL) was heated to reflux under agitation for18 h. The reaction mixture was cooled, then filtered, washed withtoluene, and dried under high vacuum. The compound is obtainedas a yellow solid (95% yield). C8H4N4O2. MW: 188.14 g/mol. Mp265-268 C. 1H NMR delta (ppm, 300 MHz, DMSO-d6) 8.24 (d, 1H,CHC-CO), 8.32 (d, 1H, CHC-CO, J3 Hz), 8.88 (d, 1H, CHN),9.28 (d, 1H, CHN, J3 Hz). 13C NMR delta (ppm, 100 MHz, DMSO-d6)123.99, 124.52, 125.62, 137.26, 139.73, 150.39, 159.68. MS (ESI+ ,QTof, m/z): 189.0 [M+H]+.
	With thionyl chloride;N,N-dimethyl-formamide; In toluene; for 30h;Heating / reflux;	Production Example 24; Production of compound (39) by the production method 8; A mixture consisting of 1.5 g (13 mmol) of 1H-imidazole-4-carboxylic acid and 5 ml of thionyl chloride and three drops of N,N-dimethylformamide and 10ml of toluene was stirred under heating and refluxing for 30 hours. After the reaction, excess thionyl chloride and the solvent were removed under reduced pressure to obtain crystal of diimidazo[1, 5-a, 1' , 5'-d] pyrazine-5,10-dione. In a separate vessel, 0.10 g (2.5 mmol) of sodium hydride was added at room temperature to a mixture consisting of 0.30 g (2.0 mmol) of 6,6-difluoro-5-methyl-5-hexenol, 0.18 g (1.0 mmol) of diimidazo[1, 5-a, 1', 5'-d]pyrazine-5,10-dione and 5 ml of tetrahydrofuran, followed by stirring at the same temperature for 2 hours, the addition of 0.40 g (2.8 mmol) of methyl iodide and further stirring for 2 hours. To the reaction liquid was added 20 ml of ethyl acetate to filter off solid and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate : methanol = 10 : 1) to obtain 0.15 g (yield: 30 %) of 6,6-difluoro-5-methyl-5-hexenyl 1-methyl-1H-imidazole-4-carboxylate.1H-NMR (CDCl3, TMS) deltappm: 1.47-1.56 (5H, m), 1.70-1.79 (2H, m), 1.98-2.04 (2H, m), 3.75 (3H, s), 4.31 (2H, t), 7.51 (2H, s), 7.56 (1H, s)

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6601 - 6610
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 909 - 919
[3]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 460 - 463
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 799 - 802
[4]Patent: EP1439169,2004,A1 .Location in patent: Page 81-82

5
[ 61985-23-7 ]
[ 53525-65-8 ]
[ 79711-73-2 ]
[ 99560-60-8 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 306 - 309

6
[ 53525-65-8 ]
[ 74-89-5 ]
[ 53525-55-6 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 460 - 463
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 799 - 802

7
[ 53525-65-8 ]
[ 615-36-1 ]
[ 69147-97-3 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 6915 - 6918

8
[ 17325-26-7 ]
[ 53525-65-8 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 306 - 309

9
[ 13189-13-4 ]
[ 53525-65-8 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 306 - 309

10
[ 53525-65-8 ]
[ 95-00-1 ]
[ 111074-70-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 303 - 307

12
[ 6298-19-7 ]
[ 53525-65-8 ]
[ 240815-48-9 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 4517 - 4529

13
[ 62476-56-6 ]
[ 53525-65-8 ]
[ 240815-51-4 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 4517 - 4529

14
[ 7321-93-9 ]
[ 53525-65-8 ]
N-(2,4-dichloro-5-pyridinyl)-1H-imidazole-4-carboxamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299

15
[ 53525-65-8 ]
[ 348-54-9 ]
N-(2-fluoroanilino)-1H-imidazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		To 2-fluoroaniline (5.45 mL, 56.5 mmol) in THF (28 mL) cooled ina -10 C bath, sodium bis(trimethylsilyl) amide (141 mL, 141 mmol,1.0 M) in THF was added. After stirring for 1 h, a suspension of 9(4.83 g, 25.6 mmol) in THF (32 mL) was added. The mixture wasallowed to warm to room temperature and stirred for 2 h. Aceticacid was added to pH 7. The reaction mixture was concentrated invacuum, followed by the addition of water and saturated aqueousNaHCO3 solution. The solid was collected by filtration, washed withdistilled water and cyclohexane, and dried under high vacuum. Thecompound is obtained as a beige solid (40% yield). C10H8FN3O. MW:205.19 g/mol. Mp 186-189 C. 1H NMR delta (ppm, 300 MHz, DMSO-d6)7.11 to 7.33 (m, 3H), 7.84 (s, 1H, N-CH= ), 7.85 (s, 1H, -CH=N), 8.12(td, 1H, -CH=C, J=9 Hz), 9.48 (s, 1H, NH). 13C NMR delta (ppm, 100 MHz,DMSO-d6) 115.70, 121.41, 123.19, 124.00, 125.20, 126.65, 136.67,152.08, 155.31, 160.75. MS (ESI+ , QTof, m/z): 205.8 [M+H]+.

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6601 - 6610
[3]European Journal of Medicinal Chemistry,2017,vol. 138,p. 909 - 919

16
[ 53525-65-8 ]
[ 367-24-8 ]
[ 357647-43-9 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3153 - 3156

17
[ 53525-65-8 ]
[ 452-92-6 ]
[ 357647-44-0 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3153 - 3156

18
[ 53525-65-8 ]
(5-bromo-2-fluoro-benzyl)-(2,4-dimethoxy-benzyl)-amine [ No CAS ]
3H-imidazole-4-carboxylic acid (5-bromo-2-fluoro-benzyl)-(2,4-dimethoxy-benzyl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299

19
[ 56460-32-3 ]
[ 53525-65-8 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4297 - 4299

20
[ 53525-65-8 ]
[ 367-25-9 ]
N-(2,4-Difluorophenyl)-1H-imidazole-5-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3153 - 3156

21
[ 53525-65-8 ]
[ 2924-09-6 ]
3H-imidazole-4-carboxylic acid (5-bromo-2-fluoro-phenyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3153 - 3156

22
[ 53525-65-8 ]
[ 112279-60-4 ]
3H-imidazole-4-carboxylic acid (4-bromo-2,5-difluoro-phenyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3153 - 3156

23
[ 1072-84-0 ]
[ 53525-65-8 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 457 - 460

24
[ 53525-65-8 ]
[ 74-89-5 ]
[ 53525-55-6 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 457 - 460

25
[ 53525-65-8 ]
N₁-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide [ No CAS ]
[ 110-16-7 ]
trans N₁-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; toluene;	Example 559 Trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate A mixture of N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide (0.200 g, 0.00041 mol) in toluene (10 mL) was reacted with <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> (0.040 g, 0.00021 mol) at reflux for 18 hours. An additional equivalent of <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> was added and the mixture was refluxed an additional 6 hours. The solvent was removed in vacuo and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give the free base (0.103 g, 0.00017 mol). The free base was dissolved in absolute ethanol (10 mL) and heated to reflux. After addition of a solution of maleic acid (0.030 g, 0.00034 mol) in absolute ethanol (1 mL) the solution was refluxed for 15 minutes, after which time a precipitate formed. The mixture was cooled to ambient temperature, and the resulting precipitate was filtered, washing with a minimal amount of absolute ethanol. The precipitate was dried in vacuo to give trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate as a white solid (0.055 g, 0.00008 mol): 1H NMR (DMSO-d6, 400 MHz) delta 9.63 (s, 1H), 8.26 (s, 1H), 8.22 (d, 1H), 8.00 (b, 1H), 7.74 (b, 1H), 7.43-7.48 (m, 1H), 7.16-7.33(m, 7H), 6.21 (s, 2H), 4.97-5.13 (m, 1H), 2.91-3.47 (m, 4H), 2.53-2.65 (m, 1H), 2.30-2.45 (m, 1H), 2.07-2.26 (m, 2H), 1.95-2.07 (m, 2H), 1.45-1.50 (m, 1H), 1.28-1.32 (m, 1H); RP-HPLC (Delta Pak C18, 5 mum, 300 A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 14.17 min.; MS: MH+ 578.
	In ethanol; toluene;	Trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate A mixture of N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide (0.200 g, 0.00041 mol) in toluene (10 mL) was reacted with <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> (0.040 g, 0.00021 mol) at reflux for 18 hours. An additional equivalent of <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> was added and the mixture was refluxed an additional 6 hours. The solvent was removed in vacuo and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give the free base (0.103 g, 0.00017 mol). The free base was dissolved in absolute ethanol (10 mL) and heated to reflux. After addition of a solution of maleic acid (0.030 g, 0.00034 mol) in absolute ethanol (1 mL) the solution was refluxed for 15 minutes, after which time a precipitate formed. The mixture was cooled to ambient temperature, and the resulting precipitate was filtered, washing with a minimal amount of absolute ethanol. The precipitate was dried in vacuo to give trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate as a white solid (0.055 g, 0.00008 mol): 1H NMR (DMSO-d6, 400 MHz) delta 9.63 (s, 1H), 8.26 (s, 1H), 8.22 (d, 1H), 8.00 (b, 1H), 7.74 (b, 1H), 7.43-7.48 (m, 1H), 7.16-7.33(m, 7H), 6.21 (s, 2H), 4.97-5.13 (m, 1H), 2.91-3.47 (m, 4H), 2.53-2.65 (m, 1H), 2.30-2.45 (m, 1H), 2.07-2.26 (m, 2H), 1.95-2.07 (m, 2H), 1.45-1.50 (m, 1H), 1.28-1.32 (m, 1H);

Reference： [1]Patent: US6921763,2005,B2
[2]Patent: US6921763,2005,B2

26
[ 53525-65-8 ]
[ 6373-46-2 ]
3H-imidazole-4-carboxylic acid (4-benzyloxyphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	for 0.5h;Steam bath;	An intimate mixture of 4.25 g (22 mmol) of 5-H, 10H-diimidazo[1,5-a, 1',5'-d]pyrazine-5,10-dione and 9.04 g (45 mmol) of 4-benzyloxyaniline was heated on a steam bath for 30 min. The residue was flash chromatographed with 5% MeOH in CH2Cl2 to give 4.8 g of the title compound (66% yield). MS m/z 294 (MH+). 1H NMR(CDCl3) delta 5.07 (s, 2H), 7.0 (d, 2H), 7.30-7.50 (m, 3H), 7.7-7.8 (m, 4H), 9.8 (s 1H), 12.6 (s, 1 H).
66%	for 0.5h;Steam bath;	A. 3-H-Imidazole-4-carboxylic acid (4-benzyloxyphenyl) amide. An intimate mixture of 4.25 g (22 mmol) of 5-H, 10H-diimidazo [1,5-a, 1', 5'- d] pyrazine-5, 10-dione and 9.04 g (45 mmol) of 4-benzyloxyaniline was heated on a steam bath for 30 min. The residue was flash chromatographed with 5% MeOH in CH2CI2 to give 4. 8 g of the title compound (66% yield). MS m/z 294 (MH+). 1H NMR (CDCl3)No. 5.07 (s, 2H), 7.0 (d, 2H), 7.30-7. 50 (m, 3H), 7.7-7. 8 (m, 4H), 9.8 (s 1H), 12.6 (s, 1H).

Reference： [1]Patent: US2005/182108,2005,A1 .Location in patent: Page/Page column 14
[2]Patent: WO2005/84663,2005,A1 .Location in patent: Page/Page column 42

27
N₁-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide [ No CAS ]
[ 53525-65-8 ]
N₁-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 24h;Heating / reflux;	[0666] A mixture of N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide (0.200 g, 0.00041 mol) in toluene (10 mL) was reacted with <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> (0.040 g, 0.00021 mol) at reflux for 18 hours. An additional equivalent of <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> was added and the mixture was refluxed an additional 6 hours. The solvent was removed in vacuo and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 mL/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give the free base (0.103 g, 0.00017 mol). The free base was dissolved in absolute ethanol (10 mL) and heated to reflux. After addition of a solution of maleic acid (0.030 g, 0.00034 mol) in absolute ethanol (1 mL) the solution was refluxed for 15 minutes, after which time a precipitate formed. The mixture was cooled to ambient temperature, and the resulting precipitate was filtered, washing with a minimal amount of absolute ethanol. The precipitate was dried in vacuo to give trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate as a white solid (0.055 g, 0.00008 mol): [0667] 1H NMR (DMSO-d6, 400 MHz) delta 9.63 (s, 1H), 8.26 (s, 1H), 8.22 (d, 1H), 8.00 (b, 1H), 7.74 (b, 1H), 7.43-7.48 (m, 1H), 7.16-7.33(m, 7H), 6.21 (s, 2H), 4.97-5.13 (m, 1H), 2.91-3.47 (m, 4H), 2.53-2.65 (m, 1H), 2.30-2.45 (m, 1H), 2.07-2.26 (m, 2H), 1.95-2.07 (m, 2H), 1.45-1.50 (m, 1H), 1.28-1.32 (m, 1H); RP-HPLC (Delta Pak C18, 5 mum, 300A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 14.17 min.; MS: MH+ 578.

Reference： [1]Patent: US2004/6083,2004,A1 .Location in patent: Page/Page column 61

28
[ 53525-65-8 ]
N₁-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide [ No CAS ]
[ 110-16-7 ]
trans N₁-(4-{4-amino-1-[I-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate [ No CAS ]
trans N₁-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; toluene;	Trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate A mixture of N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide (0.200 g, 0.00041 mol) in toluene (10 mL) was reacted with <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> (0.040 g, 0.00021 mol) at reflux for 18 hours. An additional equivalent of <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> was added and the mixture was refluxed an additional 6 hours. The solvent was removed in vacuo and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give the free base (0.103 g, 0.00017 mol). The free base was dissolved in absolute ethanol (10 mL) and heated to reflux. After addition of a solution of maleic acid (0.030 g, 0.00034 mol) in absolute ethanol (1 mL) the solution was refluxed for 15 minutes, after which time a precipitate formed. The mixture was cooled to ambient temperature, and the resulting precipitate was filtered, washing with a minimal amount of absolute ethanol. The precipitate was dried in vacuo to give trans N1-(4-{4-amino-1-[I-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate as a white solid (0.055 g, 0.00008 mol): 1H NMR (DMSO-d6, 400 MHz) delta 9.63 (s, 1H), 8.26 (s, 1H), 8.22 (d, 1H), 8.00 (b, 1H), 7.74 (b, 1H), 7.43-7.48 (m, 1H), 7.16-7.33(m, 7H), 6.21 (s, 2H), 4.97-5.13 (m, 1H), 2.91-3.47 (m, 4H), 2.53-2.65 (m, 1H), 2.30-2.45 (m, 1H), 2.07-2.26 (m, 2H), 1.95-2.07 (m, 2H), 1.45-1.50 (m, 1H), 1.28-1.32 (m, 1H); RP-HPLC (Delta Pak C18, 5 mum, 300 A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) R 14.17 min.; MS: MH+ 578.

Reference： [1]Patent: US2002/156081,2002,A1

29
[ 53525-65-8 ]
N₁-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide [ No CAS ]
OH-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione [ No CAS ]
[ 110-16-7 ]
trans N₁-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; toluene;	Trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate A mixture of N1-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-phenyl-1-cyclopropanecarboxamide (0.200 g, 0.00041 mol) in toluene (10 mL) was reacted with <strong>[53525-65-8]5H,10H-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione</strong> (0.040 g, 0.00021 mol) at reflux for 18 hours. An additional equivalent of 5H,1OH-diimidazo[1,5-a:1,5-d]pyrazine-5,10-dione was added and the mixture was refluxed an additional 6 hours. The solvent was removed in vacuo and the residue was purified by preparative RP-HPLC (Rainin C18, 8 mum, 300 A, 25 cm; 30% isocratic for five minutes, then 30%-60% acetonitrile-0.1M ammonium acetate over 15 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give the free base (0.103 g, 0.00017 mol). The free base was dissolved in absolute ethanol (10 mL) and heated to reflux. After addition of a solution of maleic acid (0.030 g, 0.00034 mol) in absolute ethanol (1 mL) the solution was refluxed for 15 minutes, after which time a precipitate formed. The mixture was cooled to ambient temperature, and the resulting precipitate was filtered, washing with a minimal amount of absolute ethanol. The precipitate was dried in vacuo to give trans N1-(4-{4-amino-1-[1-(1H-2-imidazolylcarbonyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-(trans)-2-phenyl-1-cyclopropanecarboxamide maleate as a white solid (0.055 g, 0.00008 mol): 1H NMR (DMSO-d6 400 MHz) delta 9.63 (s, 1H), 8.26 (s, 1H), 8.22 (d, 1H), 8.00 (b, 1H), 7.74 (b, 1H), 7.43-7.48 (m, 1H), 7.16-7.33(m, 7H), 6.21 (s, 2H), 4.97-5.13 (m, 1H), 2.91-3.47 (m, 4H), 2.53-2.65 (m, 1H), 2.30-2.45 (m, 1H), 2.07-2.26 (m, 2H), 1.95-2.07 (m, 2H), 1.45-1.50 (m, 1H), 1.28-1.32 (m, 1H);

Reference： [1]Patent: US2002/156081,2002,A1

30
[ 53525-65-8 ]
trans-4-amino-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide [ No CAS ]
[ 67-66-3 ]
[ 67765-42-8 ]
[ 121-44-8 ]
trans-3-hydroxy-4-[(1H-imidazol-5-yl)carbonylamino]-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.13 parts (23%)	In methanol; N,N-dimethyl-formamide;	EXAMPLE 12 2.8 Parts of N,N-diethylethanamine were added to a solution of 1 part of 5H, 10H-diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione in 36 parts of N,N-dimethylformamide. The thus obtained suspension was added dropwise to a stirred and heated (70 C.) solution of 3.95 parts of trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide in 18 parts of N,N-dimethylformamide. Upon complete addition, stirring was continued overnight at 70 C. After evaporation, the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was further purified by column chromatography (HPLC) over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (90:9:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was pulverised and evaporated again, yielding 1.13 parts (23%) of trans-3-hydroxy-4-[(1H-imidazol-5-yl)carbonylamino] -N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide; mp. 155.0 C. (compound 43).

Reference： [1]Patent: US4990521,1991,A

31
[ 53525-65-8 ]
[ 1123515-40-1 ]
[ 1123512-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 100℃; for 24h;	Nl-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-yl)-4-methylbenzene-l,3-diamine 29a (0.1 mmol) and 5H,10H-diimidazo[l,5-a:l' ,5'-d]pyrazine-5,10-dione (0.1 mmol) in dry DMF (0.5 mL) are heated at 110 0C for 24 h. HPLC purification affords the target compound B7 as a TFA salt. 1H NMR (400MHz, J6-DMSO) delta 9.80 (s, 2H), 8.81 (s, 2H), 8.44 (s, IH), 8.04 (s, 2H), 7.77 (d, J = 8.8 Hz, 2H), 7.57 (m, IH), 7.28 (t, J = 74.0 Hz, IH), 7.27 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 8.4 Hz, IH), 2.20 (s, 3H). MS (m/z) (M+l)+: 437.2.

Reference： [1]Patent: WO2009/26276,2009,A1 .Location in patent: Page/Page column 66

32
[ 53525-65-8 ]
[ 765-30-0 ]
[ 869491-11-2 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5243 - 5263

33
[ 6298-19-7 ]
[ 53525-65-8 ]
[ 240815-48-9 ]

Yield	Reaction Conditions	Operation in experiment
		To 3-amino-2-chloropyridine (2.87 g, 22.3 mmol) in THF (13 mL) cooled in a -10C bath was added sodium hexamethyldisilazide (51 mL, 51 mmol, 1M in THF). The mixture was stirred for 1 hr, then a suspension of imidazole carbonyl dimer (2 g, 10.6 mmol, see 15 in Scheme III above) in THF (20 mL) was added and let warm to room temperature. The mixture was stirred for 2 h then quenched with acetic acid. The reaction was concentrated in vacuo followed by the addition of water and saturated sodium bicarbonate. The solid product was collected by filtration with a water and hexane wash, then dried in vacuo to give the desired product 1A.

Reference： [1]Patent: EP1066286,2009,B1 .Location in patent: Page/Page column 21

34
[ 62476-56-6 ]
[ 53525-65-8 ]
[ 240815-51-4 ]

Yield	Reaction Conditions	Operation in experiment
		To 3-amino-2,6-dichloropyridine (0.28 g, 1.7 mmol) in THF (1.4 mL) cooled in an ice/MeOH bath was added sodium hexamethyldisilazide (3.4 mL, 3.4 mmol). The mixture was stirred for 0.5 h followed by the addition of imidazole carbonyl dimer (0.16 g, 0.86 mmol) in THF (2 mL). The reaction was warmed to room temperature for 15 min then quenched with acetic acid. The reaction was concentrated in vacuo, then water and saturated sodium bicarbonate was added. The solid product was isolated by filtration with water and hexane rinses, then dried in vacuo to yield 7A.

Reference： [1]Patent: EP1066286,2009,B1 .Location in patent: Page/Page column 23-24

35
[ 53525-65-8 ]
[ 509101-24-0 ]
[ 74-88-4 ]
6,6-difluoro-5-methyl-5-hexenyl 1-methyl-1H-imidazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		A mixture consisting of 1.5 g (13 mmol) of 1H-imidazole-4-carboxylic acid and 5 ml of thionyl chloride and three drops of N,N-dimethylformamide and 10ml of toluene was stirred under heating and refluxing for 30 hours. After the reaction, excess thionyl chloride and the solvent were removed under reduced pressure to obtain crystal of diimidazo[1, 5-a, 1' , 5'-d] pyrazine-5,10-dione. In a separate vessel, 0.10 g (2.5 mmol) of sodium hydride was added at room temperature to a mixture consisting of 0.30 g (2.0 mmol) of 6,6-difluoro-5-methyl-5-hexenol, 0.18 g (1.0 mmol) of diimidazo[1, 5-a, 1', 5'-d]pyrazine-5,10-dione and 5 ml of tetrahydrofuran, followed by stirring at the same temperature for 2 hours, the addition of 0.40 g (2.8 mmol) of methyl iodide and further stirring for 2 hours. To the reaction liquid was added 20 ml of ethyl acetate to filter off solid and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate : methanol = 10 : 1) to obtain 0.15 g (yield: 30 %) of 6,6-difluoro-5-methyl-5-hexenyl 1-methyl-1H-imidazole-4-carboxylate.1H-NMR (CDCl3, TMS) deltappm: 1.47-1.56 (5H, m), 1.70-1.79 (2H, m), 1.98-2.04 (2H, m), 3.75 (3H, s), 4.31 (2H, t), 7.51 (2H, s), 7.56 (1H, s)

Reference： [1]Patent: EP1439169,2004,A1 .Location in patent: Page 81-82

36
[ 53525-65-8 ]
[ 32677-01-3 ]
[ 76-05-1 ]
(S)-2-(1H-imidazole-5-carboxamido)pentanedioic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%		a) Synthesis of (S)-2-(lH-imidazole-5-carboxamido)pentanedioic acid TFA (S)-2-(1 H-imidazole-5- carboxamido)pentanedioic acid Diimidazo[l,5-a]piperazine-5,10-dione 376 mg (2 mmol) was dissolved in 20 mL dry THF. H-Glu(Oi-Bu)Oi-Bu HCI 1.2 g (4 mmol) and triethyl amine 3 mL (20 mmol) were added to the solution at 0 C and the reaction was stirred overnight at room temperature. After the solvent was removed under vacuum, the tert-butyl protected intermediate was obtained by flash column chromatography. Then, this intermediate was dissolved in 5 mL TFA/DCM(1/1) for 2 hours at room temperature. After all the solvent was removed under vacuum, compound (S)-2-(lH-imidazole-5- carboxamido) pentanedioic acid was purified by HPLC as a white powder 310 mg, yield 23 %. 1H NMR (400 MHz, D20): delta 8.69 (s,lH), 7.91 (s, 1H), 4.47 (dd, Jl = 7.2 Hz, J2 = 3.9 Hz, 1H), 2.38 (t, 7 = 5.4 Hz, 2H), 2.20-2.11(m, 1H), 2.01-1.94(m, 1H) 13C NMR (100 MHz, D20): 5177.0, 174.6, 162.8(q, TFA), 158.7, 135.5, 126.6, 120.7, 116.4 (q, TFA), 52.4, 29.8, 25.6; HPLC (Waters Atlantis, MeCN/H20 8/92, 10 mL/min): 9.5 min.

Reference： [1]Patent: WO2014/182538,2014,A1 .Location in patent: Page/Page column 27

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H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 53525-65-8 ] {[proInfo.proName]}

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[ 53525-65-8 ] Synthesis Path-Upstream 1~6

[ 53525-65-8 ] Synthesis Path-Downstream 1~36

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