[ CAS No. 96219-87-3 ] {[proInfo.proName]}

Name: 96219-87-3|(3-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanone|95%
Brand: Ambeed
SKU: A222869
Price: 19.0 USD
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Quality Control of [ 96219-87-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 96219-87-3 ]

CAS No. :	96219-87-3	MDL No. :	MFCD20260223
Formula :	C₈H₇N₃OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DKSHGSCMEXOBRE-UHFFFAOYSA-N
M.W :	193.23	Pubchem ID :	11550150
Synonyms :

Calculated chemistry of [ 96219-87-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.74
TPSA :	100.01 Å²

Pharmacokinetics

GI absorption :	High
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) :	-6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	1.78
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	0.05
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	1.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.6
Solubility :	0.489 mg/ml ; 0.00253 mol/l
Class :	Soluble
Log S (Ali) :	-3.5
Solubility :	0.0613 mg/ml ; 0.000317 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.469 mg/ml ; 0.00243 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.24

Safety of [ 96219-87-3 ]

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

Application In Synthesis of [ 96219-87-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 96219-87-3 ]
Downstream synthetic route of [ 96219-87-3 ]

[ 96219-87-3 ] Synthesis Path-Upstream 1~8

1
[ 88-15-3 ]
[ 96219-87-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1641 - 1645

2
[ 34772-98-0 ]
[ 96219-87-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1641 - 1645

3
[ 96219-87-3 ]
[ 96605-65-1 ]
[ 325715-02-4 ]

Reference： [1] Patent: US6384221, 2002, B1,
[2] Patent: WO2006/44903, 2006, A1, . Location in patent: Page/Page column 11

4
[ 96219-87-3 ]
[ 325715-02-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	for 3 h; Heating / reflux	N-[(3-Dimethylaminoacryloyl)phenyl]-N-methylacetamide (129.5 g, 0.52 moles) and (5-amino-1H-pyrazol-4-yl)-thiophen-2-yl-methanone (78.0 g, 0.40 moles) were combined in acetic acid (62.5 ml) and heated to reflux. After 3 hours, TLC (9:1; dichloromethane:methanol) showed the reaction was complete. The cooled reaction mixture was diluted with water (3 L) and the resulting solid filtered and washed with water. The solid was triturated with ethyl acetate (780 ml) for two hours, filtered and dried in vacuo at 50° C. for 48 hours. Isolated N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}acetamide was obtained as a yellow solid in 90percent yield and 99percent purity. LC/MS (M+H).377 ¹H NMR (400 MHz, CDCl₃) δ ppm 8.86 (1H, d), 8.74 (1H, s), 8.12 (1H, d), 8.00 (2H, s), 7.73 (1H, d), 7.68 (1H, t), 7.49 (1H, d), 7.23 (1H, d), 7.17 (1H, d), 3.37 (3H, s), 2.02 (3H,s). ¹³C NMR (400 MHz, CDCl₃) δ ppm 179.30, 170.41, 152.15, 148.47, 147.5, 146.53, 144.94, 133.50, 131.70, 130.29, 130.06, 128.49, 127.91, 111.17, 109.46, 37.23, 22.65.

Reference： [1] Patent: US2008/45547, 2008, A1, . Location in patent: Page/Page column 11

5
[ 96219-87-3 ]
[ 325715-02-4 ]

Reference： [1] Patent: US2012/28045, 2012, A1,
[2] Patent: US2012/28045, 2012, A1,
[3] Patent: US2012/28045, 2012, A1,
[4] Patent: US2012/28045, 2012, A1,
[5] Patent: US2012/28045, 2012, A1,
[6] Patent: US2012/28045, 2012, A1,

6
[ 96219-87-3 ]
[ 325715-02-4 ]

Reference： [1] Patent: US6399621, 2002, B1,

7
[ 96219-87-3 ]
[ 110-16-7 ]
[ 325715-02-4 ]

Reference： [1] Patent: US2012/28045, 2012, A1,

8
[ 96219-87-3 ]
[ 6153-56-6 ]
[ 325715-02-4 ]

Reference： [1] Patent: US2012/28045, 2012, A1,

[ 96219-87-3 ] Synthesis Path-Downstream 1~68

1
α-[(dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrile [ No CAS ]
[ 96219-87-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide; aminoguanidine nitrate; In ethanol; for 6.0h;Heating / reflux;	To a mixture of aminoguanidine nitrate (17.1, 125 mmol) and 5 (20.6 g, 100 mmol) in absolute ethanol (120 ML) was added ION NaOH. The reaction mixture was refluxed for 6 hours and the solvents were removed at reduced pressure on a rotary evaporator.. water (250 ML) was added and an initial precipitate formed and was filtered (13.3 g, 68.8 mmol, 69%).. On further standing, the aqueous layer deposited an additional quantity of the desired compound 6 (3.42 g, 17.7 mmol, 18%).. Compound 6 was obtained as a tan solid (total 16.72 g, 86.5 mmol, 87%). GC/MS, m/z = 193 at TR = 13.67 min (100%). LC/MS, [M+H]' = 194

Reference： [1]Patent: EP1214075,2004,B1 .Location in patent: Page/Page column 23; 24
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

2
[ 96219-87-3 ]
(Z)-3-Dimethylamino-1-(3-nitro-phenyl)-propenone [ No CAS ]
[ 850786-63-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

3
[ 78089-99-3 ]
[ 96219-87-3 ]
[ 931114-22-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

4
[ 153813-81-1 ]
[ 96219-87-3 ]
[ 931114-23-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

5
3-dimethylamino-2-methyl-1-(3-nitro-phenyl)-propenone [ No CAS ]
[ 96219-87-3 ]
[ 931114-20-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

6
[ 1056165-76-4 ]
[ 96219-87-3 ]
[ 931114-19-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

7
[ 1006062-94-7 ]
[ 96219-87-3 ]
[ 1006062-90-3 ]

Yield	Reaction Conditions	Operation in experiment
88%		Preparative example 13: N-{2-methyl-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide; A mixture of 0.074 g (0.38 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.1 g (0.38 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-methyl-phenyl]-N-methyl-acetamide in 10 mL of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 mL of dichloromethane. The organic layers were washed with 10 mL of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 132 mg of N-{2-methyl-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 88%). 1H NMR (400 MHz, CDCl3): delta 1.87 (3H, s), 2.37 (3H, s), 3.25 (3H, s), 7.13 (1 H, d, J = 4 Hz), 7.18-7.20 (1 H, m), 7.54 (1 H, D, J = 7.6 Hz), 7.70 (1 H, d, J = 5.2 Hz), 7.94-7.98 (2H, m), 8.08 (1 H, d, J = 2.8 Hz), 8.71 (1 H, s), 8.81 (1H, d, J = 4 Hz). MS (ES) m/z= 391 (MH+) HPLC = 98.3%

Reference： [1]Patent: EP1884516,2008,A1 .Location in patent: Page/Page column 13

8
[ 1006062-95-8 ]
[ 96219-87-3 ]
[ 1006062-91-4 ]

Yield	Reaction Conditions	Operation in experiment
92%		Preparative example 14: N-{2-methoxy-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide; A mixture of 0.070 g (0.36 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.1 g (0.38 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-methoxy-phenyl]-N-methyl-acetamide in 10 mL of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 mL of dichloromethane. The organic layers were washed with 10 mL of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 135 mg of N-{2-methoxy-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 92%). 1H NMR (400 MHz, CDCl3): delta 1.90 (3H, s), 3.23 (3H, s), 3.97 (3H, s), 7.12 (1 H, d, J = 4.8 Hz), 7.17-7.21 (2H, m), 7.70 (1 H, d, J = 4.4 Hz), 8.02 (1 H, S), 8.09 (1 H, d, J = 4 Hz),8.15 (1 H, d, J = 8.8 Hz), 8.71 (1 H, s), 8.79 (1 H, d, J = 4.4 Hz). MS (ES) m/z = 407 (MH+) HPLC = 100%

Reference： [1]Patent: EP1884516,2008,A1 .Location in patent: Page/Page column 14

9
[ 1006062-96-9 ]
[ 96219-87-3 ]
[ 1006062-92-5 ]

Yield	Reaction Conditions	Operation in experiment
69%		Preparative example 15: N-{2,4-difluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide; A mixture of 0.217 g (1.12 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.3 g (1.12 mmol) of N-[5-(3-dimethylamino-acryloyl)-2,4-difluoro-phenyl]-N-methyl-acetamide in 10 mL of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 mL of dichloromethane. The organic layers were washed with 10 mL of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 320 mg of N-{2,4-difluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 69%). 1H NMR (250 MHz, CDCl3): delta 1.82 (3H, s), 3.11 (3H, s), 6,96-7,06 (3H, m), 7,55 (1 H, d, J = 4,9 Hz), 7.76 (1 H, t, J = 8,2 Hz), 7.91 (1 H, dd, J = 1 and 3.6 Hz), 8.52 (1 H, s), 8.68 (1 H, d, J = 4.1 Hz). MS (ES) m/z = 413 (MH+) HPLC = 99.0%

Reference： [1]Patent: EP1884516,2008,A1 .Location in patent: Page/Page column 14

10
[ 88-15-3 ]
[ 96219-87-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

11
[ 34772-98-0 ]
[ 96219-87-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

12
[ 96219-87-3 ]
[ 931114-27-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

13
[ 96219-87-3 ]
[ 931114-28-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

14
[ 96219-87-3 ]
[ 931114-26-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

15
[ 96219-87-3 ]
[ 879373-60-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

16
[ 96219-87-3 ]
3-methyl-N-{4-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-butyramide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

17
[ 96219-87-3 ]
{3-[5-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-carbamic acid isopropyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

18
[ 96219-87-3 ]
3-methyl-N-{2-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-butyramide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

19
[ 96219-87-3 ]
{3-[6-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-carbamic acid isopropyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

20
[ 96219-87-3 ]
cyclopropanecarboxylic acid {3-[5-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

21
[ 96219-87-3 ]
1-isopropyl-3-{3-[5-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

22
[ 96219-87-3 ]
3-methyl-N-{3-[6-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-butyramide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

23
[ 96219-87-3 ]
3-methyl-N-{3-[5-methyl-3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}butanamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

24
[ 96219-87-3 ]
1-isopropyl-3-{3-[6-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

25
[ 96219-87-3 ]
cyclopropanecarboxylic acid {3-[6-methyl-3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1641 - 1645

26
[ 96219-87-3 ]
[ 850786-64-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

27
[ 96219-87-3 ]
N-{3-[3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}propane-2-sulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

28
[ 96219-87-3 ]
{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-carbamic acid isopropyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

29
[ 96219-87-3 ]
[ 850786-65-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

30
[ 96219-87-3 ]
1-isopropyl-3-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

31
[ 96219-87-3 ]
cyclopropanecarboxylic acid ethyl-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

32
[ 96219-87-3 ]
{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-carbamic acid butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

33
[ 96219-87-3 ]
N-neopentyl-N'-{3-[3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

34
[ 96219-87-3 ]
N-cyclopropyl-N'-{3-[3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

35
[ 96219-87-3 ]
N-Butyl-N'-{3-[3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl}urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

36
[ 96219-87-3 ]
{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-carbamic acid 4-nitro-phenyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1591 - 1594

37
[ 844679-41-0 ]
[ 96219-87-3 ]
N-ethyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.6%		Example 6: N-ETHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-METHANESULFONAMIDE A mixture of 0.36 g (1.86 mmol) of 5-AMINO-LH-PYRAZOL-4- yl) -thiophene-2-yl-methanone and 0.55 g (1.86 mmol) of N- [3- [3- (dimethylamino)-l-oxo-2-propenyl] phenyl]-N-ethyl- methane sulfonamide in 10 ml of glacial acetic acid was refluxed for 8 hours. Thereafter, the reaction mixture was cooled and the precipitate formed, which was filtered, was washed first with acetic acid, then with saturated sodium bicarbonate solution and finally with water. 472 mg of N- ETHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5-A] PYRIMIDIN-7-YL]-PHENYL}-METHANE-SULFONAMIDE were obtained as a yellow solid (yield 59. 6%).

Reference： [1]Patent: WO2005/14597,2005,A1 .Location in patent: Page/Page column 36

38
[ 844679-49-8 ]
[ 96219-87-3 ]
N-ethyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.4%		Example 12: N-ETHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)- pyrazolo [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-BENZENESULFONAMIDE A mixture of 0.33 g (1.70 mmol) of (5-AMINO-LH-PYRAZOL-4- yl) -thiophene-2-yl-methanone and 0.61 g (1.70 mmol) of N- [3- [3- (dimethylamino)-l-oxo-2-propenyl] phenyl]-N-ethyl- benzenesulfonamide in 10 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 10 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to drynes-s--to yield an oil which, in the presence of ethyl acetate, gave 535 mg of N-ETHYL-N-3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-BENZENESULFONAMIDE as a yellow solid (yield 64. 4%).

Reference： [1]Patent: WO2005/14597,2005,A1 .Location in patent: Page/Page column 40; 41

39
[ 844679-37-4 ]
[ 96219-87-3 ]
N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		Example 3: N-METHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)- pyrazolo [1, 5-A] PYRIMIDIN-7-YL]-PHENYL}-METHANESULFONAMIDE A mixture of 0.1 g (0.52 mmol) of (5-AMINO-LH-PYRAZOL-4- yl) -thiophene-2-yl-methanone and 0.146 g (0.93 mmol) of N- [3- [3- (dimethylamino)-l-oxo-2-propenyl] phenyl]-N-methyl- methanesulfonamide (obtained as described in Example 2) in 10 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 10 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 178 mg N-METHYL-N- {3- [3- (THIOPHENE-2- CARBONYL)-PYRAZOLO [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-METHANE- sulfonamide as a yellow solid (yield 83% ; m. P. = 169- 170C).

Reference： [1]Patent: WO2005/14597,2005,A1 .Location in patent: Page/Page column 34

40
[ 844679-45-4 ]
[ 96219-87-3 ]
N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.3%		Example 9: N-METHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)- pyrazolo [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-BENZENESULFONAMIDE A mixture of 0.43 g (2.23 mmol) of (5-AMINO-LH-PYRAZOL-4- yl) -thiophene-2-yl-methanone and 0.8 g (2.23 mmol) of N- [3- [3-(DIMETHYLAMINO)-1-OXO-2-PROPENYL] PHENYL]-N-METHYL- methane-sulfonamide in 10 ml of glacial acetic acid was refluxed for 8 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 10 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 872 g of N-METHYL-N- {3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5-a] PYRIMIDIN-7-YL]-PHENYL}-BENZENESULFONAMIDE as a yellow solid (yield 82. 3%).

Reference： [1]Patent: WO2005/14597,2005,A1 .Location in patent: Page/Page column 38; 39

41
[ 844679-62-5 ]
[ 96219-87-3 ]
N-prop-2-inyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		Example 16: General procedure for the preparation of pyrazolo [1, 5-a] pyrimidines of general formula (I) following Scheme 1 N-PROP-2-INYL-N- {3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5- a] PYRIMIDIN-7-YL]-PHENYL}-METHANESULFONAMIDE 0.1 g (0.33 mmol) of 4-THIOPHENE-2-CARBONYL-2H-PYRAZOL-3- ylamine and 0.063 g (0.33 mmol) of N- [3- [3- (DIMETHYLAMINO)- 1-OXO-2-PROPENYL] PHENYL]-N-PROP-2-INYL-METHANESULFONAMIDE were dissolved in 10 ml of glacial acetic acid. After refluxing for 8 hours, the solvent was removed by reduced pressure distillation. To the resultant residue 10 ml of dichloromethane and 10 ml of a saturated solution of sodium bicarbonate were added. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporate to dryness to yield an oil which, in the presence of ethyl acetate gave a yellow solid, 111 mg (yield= 78%) N-PROP-2-INYL-N- {3- [3- (THIOPHENE-2-CARBONYL)-PYRAZOLO [1, 5- A] PYRIMIDIN-7-YL]-PHENYL}-METHANESULFONAMIDE.

Reference： [1]Patent: WO2005/14597,2005,A1 .Location in patent: Page/Page column 55

42
[ 96219-87-3 ]
[ 115955-48-1 ]
[ 850786-63-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetic acid; for 3.0h;Heating / reflux;	A mixture of (3-amino-1H-pyrazol-4-yl)-2-thienyl-methanone (2.0 g, 10.4 mmol) and <strong>[115955-48-1]3-(dimethylamino)-1-(3-nitrophenyl)-2-propen-1-one</strong> (2.24 g, 10.4 mmol) in acetic acid (10 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and slurried with water. The thick suspension was filtered, washed thoroughly with water and dried to give 3.38 g (93%) of [7-(3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-thienyl-methanone as a white solid, mp 199-201 C.
93%	In acetic acid; for 3.0h;Heating / reflux;	A mixture of (3-amino-1H-pyrazol-4-yl)-2-thienyl-methanone (2.0 g, 10.4 mmol) and <strong>[115955-48-1]3-(dimethylamino)-1-(3-nitrophenyl)-2-propen-1-one</strong> (2.24 g, 10.4 mmol) in acetic acid (10 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and slurried with water. The thick suspension was filtered, washed thoroughly with water and dried to give 3.38 g (93%) of [7-(3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-thienyl-methanone as a white solid, mp 199-201 C.

Reference： [1]Patent: US2006/63784,2006,A1 .Location in patent: Page/Page column 43
[2]Patent: US2006/63785,2006,A1 .Location in patent: Page/Page column 48

43
[ 96219-87-3 ]
[ 1227694-88-3 ]
[ 325715-02-4 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; acetic acid	N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1.5-a]pyrimidin-7-yl]phenyl]acetamide (Compound 1) N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1.5-a]pyrimidin-7-yl]phenyl]acetamide (Compound 1) A mixture of (3-amino-1H-pyrazol-4-yl)-2-thienylmethanone (4) (1.93 g, 10 mmol) and N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (6) (2.46 g, 10 mmol) in glacial acetic acid (100 mL) is refluxed for 8 hrs. Evaporation of all volatiles on a rotary evaporator gives a residue which is partitioned between aqueous saturated sodium bicarbonate and methylene chloride. The methylene chloride layer is dried over sodium sulfate and filtered. Two additional volumes of methylene chloride are added and the solution is warmed to reflux. Hexane is added until crystallization is observed. The mixture is cooled and filtered to give Compound 1 as a yellow solid (2.57 g, 7 mmol, 70%). It will be appreciated that, although specific embodiments of the invention have been described herein for purposes of illustration, various modifications may be made without departing from the spirit and scope of the invention. Accordingly, the invention is not limited except as by the appended claims.

Reference： [1]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - US6399621, 2002, B1

44
[ 96219-87-3 ]
[ 1227694-88-3 ]
[ 67000-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In dichloromethane	32.7 Step 7 Step 7 N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide A fifty liter flask is charged with 1.936 kg of (3-amino-1H-pyrazol-4-yl)-2-thienylmethanone, 2.450 kg of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide and 33.3 kg of acetic acid (Van Waters). The reaction mixture is heated at reflux for 6 hours. The reaction mixture is evaporated to a residue under reduced pressure while maintaining the temperature at approximately 45?C. The residue is dissolved in methylene chloride (8 L; Spectrum) then precipitated by the addition of 32 L of methyl-t-butyl ether.

Reference： [1]Current Patent Assignee: PFIZER INC - US6485746, 2002, B1

45
[ 917393-51-2 ]
[ 96219-87-3 ]
N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-prop-2-ynyl-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With acetic acid; for 2.0h;Reflux;	A mixture of 0.108 g (0.56 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.198 g (0.61 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyt]-N-prop-2-ynyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 2 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 156 mg of N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-prop-2-ynyl-methanesulfonamide as a solid (yield 61%). 1H NMR(400 MHz, CDCl3): delta 2.39 (1H, s), 3.16 (3H, s,), 4.50 (2H, s), 7.14 (1H, d, J= 4.4 Hz), 7.18-7.20 (1 H, m), 7.40-7.44 (1 H, m), 7.70 (1 H, m), 8.07-8.09 (1 H, m), 8.18-8.21 (1 H, m), 8.24-8.26 (1 H, m), 8.7 (1 H, s), 8.80 (1 H, d, J= 4.8 Hz). MS (ES) m/z = 455 (MH+) HPLC = 94.9%

Reference： [1]Patent: EP1736475,2006,A1 .Location in patent: Page/Page column 15

46
[ 917393-46-5 ]
[ 96219-87-3 ]
Lorediplon [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.5%	With acetic acid; at 75.0℃; for 4.0h;	A mixture of 10 g (0.038 moles) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro- phenyl]-N-methyl-acetamide (I) and 9.6 g (0.038 moles) of (5-amino-1 H- pyrazol-4-yl)thiophene-2-yl-methanone (III) in 3OmL of glacial acetic acid was heated at 750C for 4 hours. Then, 3OmL of isopropanol were added and the precipitated solid was filtered off, washed with 9OmL of isopropanol, and dried under vacuum at 4O0C. A white-yellowish solid (12.9 g, 86.5% yield) with a melting point = 158-1590C was obtained.MS (ES) m/z = 395 (MH+)1H NMR (400 MHz, CI3CD): delta 1.92 (3H, s), 3.24 (3H, s), 7.09 (1 H, d, J = 4.4 Hz), 7.12-7.14 (1 H, m), 7.36 (1 H, t, J = 8.8 Hz), 7.64 (1 H, d, J = 4.8 Hz), 7.97- 8.01 (2H, m), 8.07 (1 H, dd, J = 2.0 Hz, J = 7.6 Hz), 8.64 (1 H, s), 8.75 (1 H, d, J = 4 Hz).HPLC = 99.7%
86.5%	With acetic acid; at 75.0℃; for 4.0h;	Example 3Synthesis of N-{2-fluoro-5-[3-(thiophene)-2-carbonyl-pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}-N-methyl-acetamide (II) A mixture of 10 g (0.038 moles) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide (I) and 9.6 g (0.038 moles) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)thiophene-2-yl-methanone</strong> (III) in 30 mL of glacial acetic acid was heated at 75 C. for 4 hours. Then, 30 mL of isopropanol were added and the precipitated solid was filtered off, washed with 90 mL of isopropanol, and dried under vacuum at 40 C. A white-yellowish solid (12.9 g, 86.5% yield) with a melting point=158-159 C. was obtained.MS (ES) m/z=395 (MH+)1H NMR (400 MHz, Cl3CD): delta 1.92 (3H, s), 3.24 (3H, s), 7.09 (1H, d, J=4.4 Hz), 7.12-7.14 (1H, m), 7.36 (1H, t, J=8.8 Hz), 7.64 (1H, d, J=4.8 Hz), 7.97-8.01 (2H, m), 8.07 (1H, dd, J=2.0 Hz, J=7.6 Hz), 8.64 (1H, s), 8.75 (1H, d, J=4 Hz).HPLC=99.7%
85%	With acetic acid; at 120.0℃; for 4.0h;	Example 1 : Polymorph B of N-{2-Fluoro-5-[3-(thiophene-2-carbonyl)- pyrazolo[1 ,5-a] pyrimidin-7-yl]-phenyl}-N-methyl-acetamideA 300 L vessel was flushed with nitrogen. Acetic acid (40.0 L) was charged, and then 7.312 kg (37.84 moles) of (5-amino-1 H-pyrazol-4-yl)-thiophen-2- yl-methanone and 10.000 kg (37.84 moles) of N-[5-(3-dimethylamino- acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide were added consecutively. The mixture was heated to 12O0C (+/-5C) with stirring. The reaction was controlled by HPLC until completion (<1 % of each starting material), which typically occurs in 4 hours. The reaction mass was cooled to 60-700C. 2- Propanol (80.0 L) was charged to reaction mixture, cooled to 40-450C and aged for at least 1 hour. The mixture was cooled over approximately 2.5 hours to 0-5C and aged for at least 2 hours. Solids were filtered and washed twice with 10.0 L of chilled 2-propanol. The solid product was dried under vacuum at 5O0C (+/- 50C) to remove residual solvents (<0.5% w/w of acetic acid and <0.5% w/w of 2-propanol). N-{2-fluoro-5-[3-(thiophene-2- carbonyl)-pyrazolo[1 ,5-a]pyhmidin-7-yl]-phenyl}-N-methyl-acetamide was obtained as a crystalline material (12.686 kg). Yield 85%. Purity >95%. <n="7"/>1H NMR(400 MHz, CDCI3): delta 1.98 (3H, s,), 3.3 (3H, s), 7.13 (1 H, d, J = 4 Hz), 7.18-7.20 (1 H, m), 7.42 (1 H, t, J = 8.8 Hz), 7.71 (1 H, d, J = 5.2 Hz), 8.02-8.08 (2H, m), 8.12 (1 H, dd, J = 2.4 and 7.6 Hz), 8.71 (1 H, s), 8.82 (1 H, d, J = 4 Hz). MS (ES) m/z = 395 (MH+)

75%

With acetic acid; for 2.5h;Reflux;

A mixture of 0.073 g (0.38 mmol) of [96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone and 0.1 g (0.38 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyt]-N-methyl-acetamide in 10 ml of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 112 mg of N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 75%). 1H NMR(400 MHz, CDCl3): delta 1.98 (3H, s,), 3.3 (3H, s), 7.13 (1H, d, J= 4 Hz), 7.18-7.20 (1 H, m), 7.42 (1 H, t, J= 8.8 Hz), 7.71 (1 H, d, J= 5.2 Hz), 8.02-8.08 (2H, m), 8.12 (1 H, dd, J= 2.4 and 7.6 Hz), 8.71 (1 H, s), 8.82 (1 H, d, J= 4 Hz). MS (ES) m/z = 395 (MH+) HPLC = 99.2%

Reference： [1]Patent: WO2010/81788,2010,A1 .Location in patent: Page/Page column 12
[2]Patent: US2011/275809,2011,A1 .Location in patent: Page/Page column 5
[3]Patent: WO2008/43799,2008,A1 .Location in patent: Page/Page column 5-6
[4]Patent: EP1736475,2006,A1 .Location in patent: Page/Page column 13

47
[ 917393-47-6 ]
[ 96219-87-3 ]
N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With acetic acid; for 1.5h;Reflux;	A mixture of 0.083 g (0.43 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.12 g (0.43 mmol) of N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyt]-N-methyl-acetamide in 12 ml of glacial acetic acid was refluxed for 1.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 139 mg of N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-acetamide as a solid (yield 79%). 1H NMR(400 MHz, CDCl3): delta 1.92 (3H, s,), 3.27 (3H, s), 7.15 (1H, d, J= 4.8 Hz), 7.19-7.21 (1 H, m), 7.70-7.71 (1 H, m), 7.73 (1 H, d, J= 8.8 Hz), 8.02 (1 H, dd, J= 2.4 and 7.6 Hz),8.06-8.07 (1 H, m), 8.12 8(1 H, d, J= 2 Hz), 8.71 (1 H, s), 8.83 (1 H, d, J= 4 Hz). MS (ES) m/z = 411 (MH+) HPLC = 99.6%

Reference： [1]Patent: EP1736475,2006,A1 .Location in patent: Page/Page column 14

48
[ 917393-48-7 ]
[ 96219-87-3 ]
N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid; for 2.5h;Reflux;	A mixture of 0.064 g (0.33 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.1 g (0.33 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyt]-N-methyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 2.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 111 mg of N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a solid (yield 77%). 1H NMR(400 MHz, CDCl3): delta 3.01 (3H, s,), 3.39 (3H, s), 7.13 (1H, d, J= 4.4 Hz), 7.18-7.20 (1 H, m), 7.36-7.41 (1 H, m), 7.70 (1 H, dd, J= 1.2 and 5.2 Hz), 8.07-8.09 (1 H, m), 8.11-8.17 (2H, m), 8.7 (1H, s), 8.80 (1H, d, J= 4.8 Hz). MS (ES) m/z = 431 (MH+) HPLC = 98.6%

Reference： [1]Patent: EP1736475,2006,A1 .Location in patent: Page/Page column 14

49
[ 917393-49-8 ]
[ 96219-87-3 ]
N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With acetic acid; for 1.5h;Reflux;	A mixture of 0.076 g (0.39 mmol) of <strong>[96219-87-3](5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone</strong> and 0.124 g (0.39 mmol) of (N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyt]-N-methyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 1.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 128 mg of N-{2-chloro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a solid (yield 73%). 1H NMR(400 MHz, CDCl3): delta 3.09 (3H, s,), 3.38 (3H, s), 7.15 (1H, d, J= 4.8 Hz), 7.19-7.20 (1 H, m), 7.68-7.71 (2H, m), 8.07-8.09 (2H, m), 8.19 (1 H, d, J= 2 Hz), 8.71 (1 H, s), 8.82 (1 H, d, J= 4.4 Hz). MS (ES) m/z = 447 (MH+) HPLC = 98.1%

Reference： [1]Patent: EP1736475,2006,A1 .Location in patent: Page/Page column 15

50
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(2-fluoro-ethyl)-acetamide [ No CAS ]
[ 96219-87-3 ]
N-(2-fluoroethyl)-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

51
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(3-fluoro-propyl)-acetamide [ No CAS ]
[ 96219-87-3 ]
N-(3-fluoro-propyl)-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

52
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(4-fluoro-butyl)-acetamide [ No CAS ]
[ 96219-87-3 ]
N-(4-fluoro-butyl)-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194
[2]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 123 - 131

53
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(3-fluoropropyl)-propionamide [ No CAS ]
[ 96219-87-3 ]
[ 1019209-61-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

54
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(3-fluoropropyl)-isobutyramide [ No CAS ]
[ 96219-87-3 ]
[ 1019209-62-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

55
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(3-hydroxypropyl)-acetamide [ No CAS ]
[ 96219-87-3 ]
[ 1019209-69-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

56
N-[3-(3-dimethylamino-acryloyl)-phenyl]-N-(4-hydroxybutyl)-acetamide [ No CAS ]
[ 96219-87-3 ]
[ 1019209-70-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

57
[ 1114471-43-0 ]
[ 96219-87-3 ]
4-fluoro-N-methyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194
[2]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 123 - 131

58
[ 1114471-40-7 ]
[ 96219-87-3 ]
[ 1019209-85-8 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 123 - 131
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

59
3-dimethylamino-1-[3-[(2-fluoroethyl)methylamino]phenyl]propenone [ No CAS ]
[ 96219-87-3 ]
7-{3-[(2-fluoroethyl)(methyl)amino]phenyl}-[pyrazolo[1,5-a]pyrimidine-3-yl](thiophen-2-yl)-methanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 1184 - 1194

60
[ 1147866-51-0 ]
[ 96219-87-3 ]
[ 1147866-55-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

61
[ 1147866-53-2 ]
[ 96219-87-3 ]
[ 1147866-57-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

62
[ 1056165-61-7 ]
[ 96219-87-3 ]
[ 879371-74-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

63
[ 1147866-54-3 ]
[ 96219-87-3 ]
[ 879373-78-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

64
[ 168618-99-3 ]
[ 96219-87-3 ]
methyl 3-[3-(2-thienylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]benzoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

65
[ 1147866-58-7 ]
[ 96219-87-3 ]
[ 1147866-61-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

66
[ 1147866-59-8 ]
[ 96219-87-3 ]
[ 879373-74-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

67
[ 1147866-60-1 ]
[ 96219-87-3 ]
[ 879371-66-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

68
(2E)-3-(dimethylamino)-1-(4-methoxy-3-nitrophenyl)prop-2-en-1-one [ No CAS ]
[ 96219-87-3 ]
[ 1147866-56-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2091 - 2100

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
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. 96219-87-3 ] {[proInfo.proName]}

Quality Control of [ 96219-87-3 ]

Related Doc. of [ 96219-87-3 ]

Product Details of [ 96219-87-3 ]

Calculated chemistry of [ 96219-87-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 96219-87-3 ]

Application In Synthesis of [ 96219-87-3 ]

[ 96219-87-3 ] Synthesis Path-Upstream 1~8

[ 96219-87-3 ] Synthesis Path-Downstream 1~68

Pharmaceutical Intermediates of [ 96219-87-3 ]

Indiplon Related Intermediates

Related Functional Groups of [ 96219-87-3 ]

Ketones

Amines

Related Parent Nucleus of [ 96219-87-3 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 96219-87-3 ]

Related Functional Groups of
[ 96219-87-3 ]

Related Parent Nucleus of
[ 96219-87-3 ]