[ CAS No. 49633-25-2 ] {[proInfo.proName]}

Name: 49633-25-2|3-Isopropylpyrazole|97%
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Product Details of [ 49633-25-2 ]

CAS No. :	49633-25-2	MDL No. :	MFCD08701139
Formula :	C₆H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZICRALLMHKILDG-UHFFFAOYSA-N
M.W :	110.16	Pubchem ID :	12251381
Synonyms :

Calculated chemistry of [ 49633-25-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.17
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.23
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.53
Log Po/w (MLOGP) :	0.72
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.79
Solubility :	1.79 mg/ml ; 0.0163 mol/l
Class :	Very soluble
Log S (Ali) :	-1.59
Solubility :	2.86 mg/ml ; 0.026 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.11 mg/ml ; 0.0101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 49633-25-2 ]

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

Application In Synthesis of [ 49633-25-2 ]

* 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 [ 49633-25-2 ]
Downstream synthetic route of [ 49633-25-2 ]

[ 49633-25-2 ] Synthesis Path-Upstream 1~7

1
[ 5782-56-9 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrazine hydrochloride; sulfuric acid In water at 68℃; for 2 h;	Step 4: Preparation of 3-isopropyl-lH-pyrazole 88b. Compound 87 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL) and H₂O (6 mL). The reaction mixture was stirred at 68 ⁰C for 2 hrs. The mixture was then neutralized with IN NaOH and extracted with diethyl ether. The organic layer was dried over Na₂SO₄, filtered, and concentrated under reduced pressure to yield compound 88b as a beige solid in 94percent yield.¹H NMR (DMSO-J₆, 400 MHz) δ 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, IH), 5.99 (s, IH), 7.40 (s, IH).1.39-1.43 (t, J = 7.04 Hz, 3H), 4.08-4.13 (q, J = 7.04 Hz, 2H), 5.86 (d, J = 12.40 Hz, IH), 7.90 (d, J = 12.40 Hz, IH).

Reference： [1] Patent: WO2009/14730, 2009, A1, . Location in patent: Page/Page column 132
[2] Patent: US2004/63744, 2004, A1, . Location in patent: Page/Page column 89
[3] Patent: WO2011/17389, 2011, A1, . Location in patent: Page/Page column 152

2
[ 2644-70-4 ]
[ 38664-64-1 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuric acid In water	Step D: Preparation of 3-isopropyl-1H-pyrazole 86b. Compound 85 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL) and H₂O (6 mL). The reaction mixture was stirred at 68° C. for 2 hrs. The mixture was then neutralized with 1N NaOH and extracted with diethyl ether. The organic layer was dried over Na₂SO₄, filtered, and concentrated under reduced pressure to yield compound 86b as a beige solid in 94percent yield. ¹H NMR (DMSO-d₆, 400 MHz) δ 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, 1H), 5.99 (s, 1H), 7.40 (s, 1H). 1.39-1.43 (t, J=7.04 Hz, 3H), 4.08-4.13 (q, J=7.04 Hz, 2H), 5.86 (d, J=12.40 Hz, 1H), 7.90 (d, J=12.40 Hz, 1H).
94%	With sulfuric acid In water	Step D: Preparation of 3-isopropyl-1H-pyrazole 233b. Compound 232 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL), and H₂O (6 mL). The reaction mixture was stirred at 68° C. for 2 hrs. The mixture was then neutralized with 1N NaOH and extracted with diethyl ether. The organic layer was dried over Na₂SO₄, filtered, and concentrated under reduced pressure to yield compound 233b as a beige solid in 94percent yield. ¹H NMR (DMSO-d₆, 400 MHz) δ (ppm) 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, 1H), 5.99 (s, 1H), 7.40 (s, 1H). 1.39-1.43 (t, J=7.04 Hz, 3H), 4.08-4.13 (q, J=7.04 Hz, 2H), 5.86 (d, J=12.40 Hz, 1H), 7.90 (d, J=12.40 Hz, 1H).

Reference： [1] Patent: US2009/202480, 2009, A1,
[2] Patent: US2010/260710, 2010, A1,

3
[ 563-80-4 ]
[ 1186-70-5 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: for 8 h; Heating / reflux Stage #2: With hydrazine In butan-1-ol for 6 h; Heating / reflux	Reference Example 314 A mixture of 3-methyl-2-butanone (10.7 ml) and bis(dimethylamino)methoxymethane (6.61 g) was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. Hydrazine monohydrate (5.80 g) and n- <Desc/Clms Page number 273>butyl alcohol (29 ml) were added to the residue and the mixture was heated under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1: 1, volume ratio) to give 3-isopropyl-lH-pyrazole (4.26 g, yield 59percent) as a colorless oil. H-NMR (CDCIs) 8 : 1.30 (6H, d, J=6.9 Hz), 2.84-3. 24 (1H, m), 6.10 (1H, d, J=2.0 Hz), 7.49 (1H, d, J=1.9 Hz), 10.3 (1H, br s).

Reference： [1] Patent: WO2003/99793, 2003, A1, . Location in patent: Page 272

4
[ 598-23-2 ]
[ 18107-18-1 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	at 135℃; for 1 h; Microwave irradiation	A mixture of 3-methyl-but-1-yne (0.40 g, 5.88 mmol) in trimethylsilanylmcthanediazonium (3 mL) was heated at 135 °C for 1 h in a microwave reactor. The mixture was concentrated at low temperature to afford 3-isopropyl-1H-pyrazole as a yellow oil (380 mg50percent).

Reference： [1] Patent: WO2017/19804, 2017, A2, . Location in patent: Paragraph 0328

5
[ 563-80-4 ]
[ 109-94-4 ]
[ 49633-25-2 ]

Reference： [1] Polyhedron, 2011, vol. 30, # 11, p. 1899 - 1905

6
[ 563-80-4 ]
[ 49633-25-2 ]

Reference： [1] Patent: WO2011/17389, 2011, A1,

7
[ 107073-66-5 ]
[ 75-26-3 ]
[ 288-13-1 ]
[ 49633-25-2 ]

Reference： [1] Heterocycles, 1986, vol. 24, # 4, p. 1075 - 1078

[ 49633-25-2 ] Synthesis Path-Downstream 1~88

1
[ 104294-50-0 ]
[ 49633-25-2 ]
[ 151803-84-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1993,vol. 112,p. 330 - 334

2
[ 107073-66-5 ]
[ 75-26-3 ]
[ 288-13-1 ]
[ 49633-25-2 ]

Reference： [1]Heterocycles,1986,vol. 24,p. 1075 - 1078

3
[ 507-20-0 ]
[ 49633-25-2 ]
4-(tert-butyl)-3-isopropylpyrazole [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 819 - 823

5
[ 100-39-0 ]
[ 49633-25-2 ]
[ 628332-24-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃; for 5h;	Reference Example 324 To a mixture of3-isopropyl-lH-pyrazole (92.5 g), potassium tert-butoxide(123 g) and tetrahydrofuran (840 ml) was added benzyl bromide (125 ml) at0 C and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried(MgS04) and concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-3-isopropyl-lH-pyrazole (114 g, yield68%) was obtained as a brown oily substance from a fraction eluted with ethyl acetate-hexane (1: 9, volume ratio). H-NMR (CDC13) 6 : 1.27 (6H, d, J=7. 2 Hz), 2.96-3. 07 (1H, m), 5.26 (2H, s), 6.06-6. 09 (1H, m), 7.02-7. 07 (1H, m), 7.14-7. 36 (5H, m).

Reference： [1]Patent: WO2003/99793,2003,A1 .Location in patent: Page 276

6
[ 563-80-4 ]
[ 1186-70-5 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
59%		Reference Example 314 A mixture of 3-methyl-2-butanone (10.7 ml) and bis(dimethylamino)methoxymethane (6.61 g) was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. Hydrazine monohydrate (5.80 g) and n- <Desc/Clms Page number 273>butyl alcohol (29 ml) were added to the residue and the mixture was heated under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1: 1, volume ratio) to give 3-isopropyl-lH-pyrazole (4.26 g, yield 59%) as a colorless oil. H-NMR (CDCIs) 8 : 1.30 (6H, d, J=6.9 Hz), 2.84-3. 24 (1H, m), 6.10 (1H, d, J=2.0 Hz), 7.49 (1H, d, J=1.9 Hz), 10.3 (1H, br s).

Reference： [1]Patent: WO2003/99793,2003,A1 .Location in patent: Page 272

7
[ 52334-81-3 ]
[ 49633-25-2 ]
[ 628332-16-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In 1-methyl-pyrrolidin-2-one; at 20℃; for 9h;	To a mixture of3-isopropyl-lH-pyrazole (3.74 g), 2- chloro-5-trifluoromethylpyridine (6.17 g) and N- methylpyrrolidone (18.7 ml) was addedNaOH (trademark: Tosoh pearl, 2.03 g) while stirring the mixture at room temperature. After reaction as it was for 9 hours, water (38 ml) and 6N hydrochloric acid (85 ml) were added, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane and then with toluene to give2- (3-isopropyl-lH-pyrazol-1-yl)-5- (trifluoromethyl) pyridine (6.94 g, yield 80%) as a colorless oil. H-NMR (CDC13)8 : 1.33 (6H, d, J=7.0 Hz), 3.0-3. 2(1H, m), 6.34(1H, d, J=2.5 Hz), 7.97(1H, dd, J=8.7, 2.1 Hz), 8.05(1H, d, J=8.7 Hz), 8.47(1H, d, J=2.5 Hz), 8.6-8. 7(1H, m).

Reference： [1]Patent: WO2003/99793,2003,A1 .Location in patent: Page 273

8
[ 49633-25-2 ]
[ 628332-22-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With ammonium cerium(IV) nitrate; iodine; In acetonitrile; at 0 - 20℃;	Reference Example 322 To a mixture of3-isopropyl-lH-pyrazole (167 g), diammonium cerium (IV) nitrate (497 g) and acetonitrile (1200 ml) was added iodine (230 g) at0 C and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium thiosulfate solution and saturated brine, dried(MgS04) and <Desc/Clms Page number 276>concentrated to give4-iodo-3-isopropyl-lH-pyrazole (254 g, yield71%) as a dark brown oily substance. H-NMR (CDC13) 6 : 1.31 (6H, d, J=6.9 Hz), 3.00-3. 17 (1H, m), 7.52 (1H, s).

Reference： [1]Patent: WO2003/99793,2003,A1 .Location in patent: Page 275

9
[ 5782-56-9 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrazine hydrochloride; sulfuric acid; In water; at 68℃; for 2h;	Step 4: Preparation of 3-isopropyl-lH-pyrazole 88b. Compound 87 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL) and H2O (6 mL). The reaction mixture was stirred at 68 0C for 2 hrs. The mixture was then neutralized with IN NaOH and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 88b as a beige solid in 94% yield.1H NMR (DMSO-J6, 400 MHz) delta 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, IH), 5.99 (s, IH), 7.40 (s, IH).1.39-1.43 (t, J = 7.04 Hz, 3H), 4.08-4.13 (q, J = 7.04 Hz, 2H), 5.86 (d, J = 12.40 Hz, IH), 7.90 (d, J = 12.40 Hz, IH).
		Compound 232 (6.6 g,1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL), and H2O (6 mL). The reaction mixture was stirred at 68 0C for 2 hrs. The mixture was then neutralized with IN NaOH and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 233b as a beige solid in 94% yield. 1H NMR (DMSO-J6, 400 MHz) delta (ppm) 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, IH), 5.99 (s, IH), 7.40 (s, 1H).1.39-1.43 (t, J= 7.04 Hz, 3H), 4.08-4.13 (q, J= 7.04 Hz, 2H), 5.86 (d, J= 12.40 Hz, IH), 7.90 (d, J= 12.40 Hz, IH).

Reference： [1]Patent: WO2009/14730,2009,A1 .Location in patent: Page/Page column 132
[2]Patent: US2004/63744,2004,A1 .Location in patent: Page/Page column 89
[3]Patent: WO2011/17389,2011,A1 .Location in patent: Page/Page column 152

10
[ 50-00-0 ]
[ 49633-25-2 ]
[ 860807-13-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; at 130℃; for 7h;	Reference Production Example 2-2 <strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong>-1-ylmethanol The mixture of 1.15 g of <strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong>, 0.94 g of paraformaldehyde and 0.14 g of triethylamine was stirred at 130 C for 7 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered. The filterate was concentrated under reduced pressure. Hexane was added to the residue, and then crystalline was formed. The crystalline was collected to obtain 1.28 g of <strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong>-1-ylmethanol. 1H-NMR(CDCl3,TMS,delta(ppm)):1.24(6H,d),2.94-3.02(1H,m),5.48(2H,s),6.10(1H,d),7.47(1H,d)

Reference： [1]Patent: EP1710234,2006,A1 .Location in patent: Page/Page column 42

11
[ 49633-25-2 ]
[ 60061-60-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bromine; sodium acetate; In water; acetic acid;	Part A - 4-Bromo-<strong>[49633-25-2]3-isopropylpyrazole</strong> To a stirred solution of sodium acetate (19.7 g., 0.24 mole) in acetic acid (100 ml.) and water (15 ml.), <strong>[49633-25-2]3-isopropylpyrazole</strong> (11.0 g., 0.1 mole) was added, followed by dropwise addition of bromine (16.0 g., 0.11 mole) keeping the internal temperature below 15 C. The mixture was kept at 25 C. for 15 hours, treated with water (200 ml.) and extracted with ethyl ether (3 * 50 ml.), and the ether layer washed with water (1 * 50 ml.) dried, (sodium sulfate) and evaporated under reduced pressure. The resultant pale yellow oil was distilled to give 4-bromo-<strong>[49633-25-2]3-isopropylpyrazole</strong> (15.3 g., 81%) with a boiling point of 85 C. at 0.06 mm Hg. Analysis: Calc'd. for C6 H9 BrN2: C, 38.11; H, 4.80; N, 14.82; Br, 42.27. Found: C, 37.91; H, 4.89; N, 14.83; Br, 42.15.
	With sodium hydroxide; bromine; In water; at 0 - 20℃; for 5h;	Reference Production Example 9-1 4-bromo-<strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong> 1.10 g of <strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong> was suspended in 20 ml of water, and 1.6 g of 50 % aqueous solution of sodium hydroxide was added to it. The mixture was cooled to 0 C, and then 1.76 g of bromine was added to the mixture, followed by stirring at room temperature for 5 hours. The reaction mixture was extracted by ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.88 g of 4-bromo-<strong>[49633-25-2]3-i-propyl-1H-pyrazole</strong>. 1H-NMR(CDCl3,TMS,delta(ppm)):1.31(6H,d),3.07-3.18(1H,m),7.49(1H,s)

Reference： [1]Patent: US3957480,1976,A
[2]Polyhedron,2011,vol. 30,p. 1899 - 1905
[3]Patent: EP1710234,2006,A1 .Location in patent: Page/Page column 48

12
1-hydroxy-4-methyl-1-pentene-3-one potassium salt [ No CAS ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine; In ethanol; for 7h;Heating / reflux;	14.14 g of 1-hydroxy-4-methyl-1-pentene-3-one potassium salt was suspended to 90 ml of ethanol. 5.11 g of hydrazine hydrate was added to the suspension, and then refluxed for 7 hours. 30 ml of water was added to the reaction mixture which was cooled to room temperature, and the mixture was concentrated to 30 ml under reduced pressure. Noushukueki was extracted by ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 6.83 g of 3-i-propyl-1H-pyrazole. 1H-NMR(CDCl3,TMS,delta(ppm)):1.29(6H,d),3.01-3.08(1H,m),6.10(1H,s),7.49(1H,s)

Reference： [1]Patent: EP1710234,2006,A1 .Location in patent: Page/Page column 41-42

13
[ 49633-25-2 ]
3-isopropyl-N,N,α-trimethylpyrazole-1-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Following the procedure of Example 36, Part B, but substituting <strong>[49633-25-2]3-isopropylpyrazole</strong> for 4-bromo-<strong>[49633-25-2]3-isopropylpyrazole</strong>, there was prepared 3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide having a boiling point at 83 C. at 0.03 mm Hg. About 10% of the 5-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide isomer was present.

Reference： [1]Patent: US3957480,1976,A

14
[ 922520-03-4 ]
[ 49633-25-2 ]
[ 922520-04-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 155℃; for 12h;	Step 7: Synthesis of 4hydroxy-2-(3-isopropylpyrazol-l-yl)-7-methoxy-8-methyl- quinoline (17).; A mixture of 4-benzyloxy-2-chloro-7-methoxy-8-methylquinoline (16, 1.00 g, 3.19 mmol) and <strong>[49633-25-2]3-isopropylpyrazole</strong> was heated at 155 0C for 12h. Then, the reaction mixture was partitioned between AcOEt and water, dried (Na2SO4) and evaporated. The residue was purified by column chromatography (AcOEtZCH2Cl2, 1:1) to give 900 mg (95 %) of the target product 17 as a yellowish powder: m/z = 298 (M + H)+.
95%	at 155℃; for 12h;	Step 7: Synthesis of 4-hydroxy-2-(3-isopropylpyrazol-l-yl)-7-methoxy-8-methyl- quinoline (64).; A mixture of 4-benzyloxy-2-chloro-7-methoxy-8-methylquinoline (63, 1.00 g, 3.19 mmol) and <strong>[49633-25-2]3-isopropylpyrazole</strong> was heated at 155 0C for 12h. Then, the reaction mixture was partitioned between AcOEt and water, dried (Na2SO4) and evaporated. The residue was purified by column chromatography (AcOEtZCH2Cl2, 1 : 1 ) to give 900 mg (95 %) of the target product 64 as a yellowish powder: m/z = 298 (M + H)+.

Reference： [1]Patent: WO2007/14925,2007,A1 .Location in patent: Page/Page column 92
[2]Patent: WO2007/14926,2007,A1 .Location in patent: Page/Page column 85
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4853 - 4858

15
[ 16940-66-2 ]
[ 49633-25-2 ]
[ 3347-62-4 ]
Na⁽¹⁺⁾*(HB((C₆H₅)(CH₃)C₃HN₂)2((CH₃)2CHC₃H₂N₂))^(1-)=Na(HB((CH₃)(C₆H₅)C₃HN₂)2)((CH₃)2CHC₃H₂N₂) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 89 - 93

16
[ 16940-66-2 ]
[ 1145-01-3 ]
[ 49633-25-2 ]
Na⁽¹⁺⁾*HB(C₃H₂(CH(CH₃)2)N₂)3^(1-)=Na(HB(C₃H₂(CH(CH₃)2)N₂)3) [ No CAS ]
Na⁽¹⁺⁾*HB((C₆H₅)2C₃HN₂)2((CH₃)2CHC₃H₂N₂)^(1-)=Na(HB((C₆H₅)2C₃HN₂)2((CH₃)2CHC₃H₂N₂)) [ No CAS ]
Na⁽¹⁺⁾*HB((C₆H₅)2C₃HN₂)3^(1-)=Na(HB((C₆H₅)2C₃HN₂)3) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 89 - 93

17
potassium borohydride [ No CAS ]
[ 49633-25-2 ]
[ 119009-96-0 ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 2211 - 2221
[2]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

18
potassium borohydride [ No CAS ]
[ 49633-25-2 ]
[ 119009-95-9 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

19
potassium borohydride [ No CAS ]
[ 49633-25-2 ]
[ 119009-97-1 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

20
Li⁽¹⁺⁾*C(CH₃)3BH₃^(1-)*0.5C₂H₅OC₂H₅=LiC(CH₃)3BH₃*0.5C₂H₅OC₂H₅ [ No CAS ]
[ 49633-25-2 ]
[ 905718-29-8 ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 5661 - 5674

21
[ 49633-25-2 ]
[ 85953-29-3 ]
[ 530091-62-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9524 - 9535

22
[ 1108659-39-7 ]
[ 49633-25-2 ]
[ 1108660-15-6 ]

Yield	Reaction Conditions	Operation in experiment
35%	In 1-methyl-pyrrolidin-2-one; at 200℃; for 0.5h;Microwave irradiation;	Step 11: Preparation of 8-chloro-4-hydroxy-7-methoxy-2-(3-isopropyl- pyrazol-l-yl)-quinoline 91c. A mixture of compounds 88b (452 mg, 4.11 mmol) and 89b (500 mg, 1.37 mmol) in N-methylpyrrolidone (2 mL) was stirred at 200 0C for 30 min under microwave irradiations. Water was then added. The reaction mixture was extracted with EtOAc, dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (DCM/EtOAc) to yield compound 91c as a white solid in 35% yield.1H NMR (DMSO-^6, 400MHz) delta 1.26 (s, 3H),1.28 (s, 3H), 2.98-3.01 (m, IH), 4.00 (s, 3H), 6.46 (m, IH), 7.16 (d, 9.32 Hz, IH), 7.89 (d, J = 9.32 Hz, IH), 8.05 (d, J = 10.85 Hz, IH), 8.60 (m, IH), 10.69 (s, IH).

Reference： [1]Patent: WO2009/14730,2009,A1 .Location in patent: Page/Page column 134

23
[ 923275-17-6 ]
[ 49633-25-2 ]
[ 923275-18-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	at 155℃; for 0.166667h;	Example 141 4-Hydroxy-2-(3-isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazoline (141) A mixture of 2-chloro-4-hydroxy-7-methoxy-8-methylquinazoline (140) (502 mg, 2.23 mmol) and <strong>[49633-25-2]3-isopropylpyrazole</strong> (500 mg, 4.55 mmol) was heated at 155 C. for 10 min. Then, the reaction mixture was successively cooled down to room temperature, partitioned between CH2Cl2 and water, dried (Na2SO4) and evaporated. The residue was triturated in ether and filtered to give the title compound (422 mg, 63%) as white needles: m/z=299 (M+H)+.

Reference： [1]Patent: US2009/118312,2009,A1 .Location in patent: Page/Page column 68

24
[ 2644-70-4 ]
[ 38664-64-1 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuric acid; In water;	Step D: Preparation of 3-isopropyl-1H-pyrazole 86b. Compound 85 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL) and H2O (6 mL). The reaction mixture was stirred at 68 C. for 2 hrs. The mixture was then neutralized with 1N NaOH and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 86b as a beige solid in 94% yield. 1H NMR (DMSO-d6, 400 MHz) delta 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, 1H), 5.99 (s, 1H), 7.40 (s, 1H). 1.39-1.43 (t, J=7.04 Hz, 3H), 4.08-4.13 (q, J=7.04 Hz, 2H), 5.86 (d, J=12.40 Hz, 1H), 7.90 (d, J=12.40 Hz, 1H).
94%	With sulfuric acid; In water;	Step D: Preparation of 3-isopropyl-1H-pyrazole 233b. Compound 232 (6.6 g, 1 eq.) was added dropwise to a stirred solution of hydrazine monochloride (3.2 g, 1 eq.), sulfuric acid (1.13 mL), and H2O (6 mL). The reaction mixture was stirred at 68 C. for 2 hrs. The mixture was then neutralized with 1N NaOH and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 233b as a beige solid in 94% yield. 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 1.17 (s, 3H), 1.19 (s, 3H), 2.87-2.93 (m, 1H), 5.99 (s, 1H), 7.40 (s, 1H). 1.39-1.43 (t, J=7.04 Hz, 3H), 4.08-4.13 (q, J=7.04 Hz, 2H), 5.86 (d, J=12.40 Hz, 1H), 7.90 (d, J=12.40 Hz, 1H).

Reference： [1]Patent: US2009/202480,2009,A1
[2]Patent: US2010/260710,2010,A1

25
[ 1108659-41-1 ]
[ 49633-25-2 ]
[ 922520-04-5 ]

Yield	Reaction Conditions	Operation in experiment
49%	In 1-methyl-pyrrolidin-2-one; diethyl ether; water;	Step H: Preparation of 4-hydroxy-7-methoxy-8-methyl-2-(3-isopropyl-pyrazol-1-yl)-quinoline 88b. A solution of compound 86b (350 mg, 1 eq.) and compound 46b (480 mg, 6 eq.) in N-methylpyrrolidone (5 mL) was heated at 200 C. for 30 min. After the reaction mixture was cooled to room temperature, water was added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (EtOAc/DCM). Recrystallisation in diethylether gave compound 88b as a white solid in 49% yield. 1H NMR (CDCl3, 376 MHz) delta 1.35 (s, 3H), 1.36 (s, 3H), 2.85 (s, 3H), 3.97 (s, 3H), 6.40 (d, J=2.65 Hz, 2H), 7.01 (d, J=9.00 Hz, 1H), 8.00 (brs, 1H), 8.23 (d, J=9.00 Hz, 1H), 9.81 (brs, 1H); MS (ESI, EI+) m/z=298 (MH+).
49%	In 1-methyl-pyrrolidin-2-one; diethyl ether; water;	Step G: Preparation of 4-hydroxy-7-methoxy-8-methyl-2-(3-isopropyl-pyrazol-1-yl)-quinoline 236b. A solution of compound 233b (350 mg, 1 eq.) and compound 221b (480 mg, 6 eq.) in N-methylpyrrolidone (5 mL) was heated at 200 C. for 30 min. After the reaction mixture was cooled to room temperature, water was added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (EtOAc/DCM). Recrystallisation in diethylether gave compound 236b as a white solid in 49% yield. 1H NMR (CDCl3, 376 MHz) delta (ppm) 1.35 (s, 3H), 1.36 (s, 3H), 2.85 (s, 3H), 3.97 (s, 3H), 6.40 (d, J=2.65 Hz, 2H), 7.01 (d, J=9.00 Hz, 1H), 8.00 (brs, 1H), 8.23 (d, J=9.00 Hz, 1H), 9.81 (brs, 1H); MS (ESI, EI+) m/z=298 (MH+).

Reference： [1]Patent: US2009/202480,2009,A1
[2]Patent: US2010/260710,2010,A1
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5427 - 5436
[4]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3984 - 3991

26
[ 563-80-4 ]
[ 49633-25-2 ]

Reference： [1]Patent: WO2011/17389,2011,A1

27
[ 1108659-39-7 ]
[ 49633-25-2 ]
[ 1265883-39-3 ]

Yield	Reaction Conditions	Operation in experiment
35%		A mixture of compound 221a (500 mg, 1.37 mmol) and compound 233b (452 mg, 4.11 mmol) in N-methylpyrrolidone (2 mL) was stirred at 200 0C for 30 min under microwave radiation. After the reaction mixture was cooled to room temperature, water was added. The reaction mixture was then extracted with EtOAc, dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (DCM/EtOAc) to yield compound 236d as a white solid in 35% yield. 1H NMR (DMSO-J6, 400 MHz) delta (ppm) 1.26 (s, 3H),1.28 (s, 3H), 2.98-3.01 (m, IH), 4.00 (s, 3H), 6.46 (m, IH), 7.16 (d, 9.32 Hz, IH), 7.89 (d, J= 9.32 Hz, IH), 8.05 (d, J= 10.85 Hz, IH), 8.60 (m, IH), 10.69 (s, IH).

Reference： [1]Patent: WO2011/17389,2011,A1 .Location in patent: Page/Page column 154

28
[ 1108659-41-1 ]
[ 49633-25-2 ]
[ 1265883-37-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	In 1-methyl-pyrrolidin-2-one; at 200℃; for 0.5h;	A solution of compound 233b (350 mg, 1 eq.) and compound 221b (480 mg, 6 eq.) in iV-methylpyrrolidone (5 mL) was heated at 2000C for 30 min. After the reaction mixture was cooled to room temperature, water was added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (EtOAc/DCM).Recrystallisation in diethylether gave compound 236b as a white solid in 49% yield. 1H- 153 -SDI-18153v2 NMR (CDCl3, 376 MHz) delta (ppm) 1.35 (s, 3H), 1.36 (s, 3H), 2.85 (s, 3H), 3.97 (s, 3H), 6.40 (d, J= 2.65 Hz, 2H), 7.01 (d, J= 9.00 Hz, IH), 8.00 (brs, IH), 8.23 (d, J= 9.00 Hz, IH), 9.81 (brs, IH); MS (ESI, EI+): m/z = 298 (MH+).

Reference： [1]Patent: WO2011/17389,2011,A1 .Location in patent: Page/Page column 153-154

29
[ 49633-25-2 ]
[ 119010-03-6 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

30
[ 49633-25-2 ]
[ 119010-04-7 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

31
[ 49633-25-2 ]
[ 119010-11-6 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

32
[ 49633-25-2 ]
[ 119010-18-3 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

33
[ 49633-25-2 ]
[ 119010-14-9 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

34
[ 49633-25-2 ]
[ 119010-15-0 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

35
[ 49633-25-2 ]
[ 119038-48-1 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

36
[ 49633-25-2 ]
[ 119038-49-2 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

37
[ 49633-25-2 ]
[ 119038-47-0 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

38
[ 49633-25-2 ]
[ 119010-12-7 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

39
[ 49633-25-2 ]
Zn(HB(C₃H₂N₂CH(CH₃)2)3)NO₃ [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

40
[ 49633-25-2 ]
[ 119009-99-3 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

41
[ 49633-25-2 ]
[ 119010-09-2 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

42
[ 49633-25-2 ]
[ 119010-13-8 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

43
[ 49633-25-2 ]
[ 119010-01-4 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

44
[ 49633-25-2 ]
[ 119010-02-5 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

45
[ 49633-25-2 ]
[ 119010-00-3 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

46
[ 49633-25-2 ]
[ 119010-10-5 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

47
[ 49633-25-2 ]
[ 119010-05-8 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

48
[ 49633-25-2 ]
[ 119010-06-9 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

49
[ 49633-25-2 ]
Zn(HB(C₃H₂N₂CH(CH₃)2)3)N₃ [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

50
[ 49633-25-2 ]
Mo(HB(C₃H₂N₂CH(CH₃)2)3)NO(CO)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

51
[ 49633-25-2 ]
[ 119010-16-1 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

52
[ 49633-25-2 ]
[ 119010-07-0 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

53
[ 49633-25-2 ]
[ 119010-08-1 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

54
[ 49633-25-2 ]
Cu(HB(C₃H₂N₂CH(CH₃)2)3)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

55
[ 49633-25-2 ]
Zn(HB(C₃H₂N₂CH(CH₃)2)3)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 1091 - 1101

56
[ 1098204-76-2 ]
[ 49633-25-2 ]
[ 1310551-70-2 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In mineral oil;	To mixture of 2,4,8-trichloro-7-(2-morpholin-4-yl-ethoxy)-quinoline (0.34 g, 0.95 mmol) and <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.63 g, 5.7 mmol) in NMP (3 ml) was added NaH (60% in mineral oil) (0.042 g, 1.05 mmol). The mixture was stirred at room temperature for over night and it monitored by LC-MS. The crude material was purified by pre-HPLC to afford 4,8-dichloro-2-(3-isopropyl-pyrazol-1-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline (0.204 g, 0.47 mmol). LC/MS=435 (M++1)

Reference： [1]Patent: US2011/135599,2011,A1

57
[ 17082-82-5 ]
[ 49633-25-2 ]
[ 1299294-02-2 ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 1699 - 1702

58
[ 563-80-4 ]
[ 109-94-4 ]
[ 49633-25-2 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 1899 - 1905

59
[ 49633-25-2 ]
[ 119009-98-2 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 1899 - 1905

60
[ 27996-13-0 ]
[ 49633-25-2 ]
[ 1332745-86-4 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 8776 - 8787
[2]Journal of Organometallic Chemistry,2011,vol. 696,p. 3623 - 3636

61
[ 49633-25-2 ]
[Li[tert-butylbis(3-tert-butylpyrazolyl)borate]2(μ-OH)]2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 5661 - 5674

62
[ 49633-25-2 ]
[ 905718-34-5 ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 5661 - 5674

63
[ 1606150-95-1 ]
[ 49633-25-2 ]
[ 1608477-11-7 ]

Yield	Reaction Conditions	Operation in experiment
16%	With caesium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide;	Step 3: 4-chloro-6-fluoro-2-(3-isopropyl-1H-pyrazol-1-yl)-7-methoxyquinoline To a stirred solution of 2,4-dichloro-6-fluoro-7-methoxyquinoline (0.2 g, 0.813 mmol) in DMF (5 mL) was added cesium carbonate (0.530 g, 1.626 mmol) followed by <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.269 g, 2.438 mmol). The reaction mixture was stirred for 12 h at 80 C. Reaction mixture was poured in water; extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate; filtered; then concentrated under reduced pressure. The resulting crude compound was purified by silica gel chromatography (1-2% ethyl acetate in pet ether) to afford 4-chloro-6-fluoro-2-(3-isopropyl-1H-pyrazol-1-yl)-7-methoxyquinoline (0.04 g, 0.13 mmol, 16%). 1H NMR (400 MHz, CDCl3): delta ppm 8.56-8.55 (dd, J=2.50, 0.50 Hz, 1H) 8.19 (d, J=0.50 Hz, 1H) 7.82-7.79 (d, J=11.76 Hz, 1H) 7.41-7.39 (d, J=8.00 Hz, 1H) 6.35 (s, 1H) 4.05 (s, 3H) 3.12-3.06 (m, 1H) 1.35-1.33 (d, 6H). MS: MS m/z 320.4 (M++1).
16%	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;	To a stirred solution of 2,4-dichloro-6-fluoro-7-methoxyquinoline (0.2 g, 0.813 mmol) in DMF (5 mL) was added cesium carbonate (0.530 g, 1.626 mmol) followed by <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.269 g, 2.438 mmol). The reaction mixture was stirred for 12 h at 80 C. Reaction mixture was poured in water; extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate; filtered; then concentrated under reduced pressure. The resulting crude compound was purified by silica gel chromatography (1-2% ethyl acetate in pet ether) to afford 4-chloro-6-fluoro-2-(3-isopropyl-1H-pyrazol-1-yl)-7-methoxyquinoline (0.04 g, 0.13 mmol, 16%). 1H NMR (400 MHz, CDCl3): delta ppm 8.56-8.55 (dd, J=2.50, 0.50 Hz, 1H) 8.19 (d, J=0.50 Hz, 1H) 7.82-7.79 (d, J=11.76 Hz, 1H) 7.41-7.39 (d, J=8.00 Hz, 1H) 6.35 (s, 1H) 4.05 (s, 3H) 3.12-3.06 (m, 1H) 1.35-1.33 (d, 6H). MS: MS m/z 320.4 (M++1).

Reference： [1]Patent: US2014/127156,2014,A1 .Location in patent: Page/Page column
[2]Patent: US9643999,2017,B2 .Location in patent: Page/Page column 22; 23

64
2,4-dichloro-7-methoxyisoquinolin [ No CAS ]
[ 49633-25-2 ]
[ 1608477-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide;	Step 1: Preparation of 4-chloro-2-(3-isopropyl-1H-pyrazol-1-yl)-7-methoxyquinoline To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.54 g, 2.36 mmol) in DMF (5 ml) was added Cs2CO3 (1.54 g, 4.74 mmol) followed by <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.78 g, 7.10 mmol). The reaction mixture was heated to 80 C. for 18 h. The reaction mass was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure to get crude compound. The crude compound was silica gel chromatography to get desired compound (0.1 g, 14%) as white solid. 1H NMR (400 MHz, CDCl3): delta ppm 8.60 (d, J=2.51 Hz, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 7.26 (s, 2H) 7.16-7.22 (m, 1H) 6.35 (d, J=2.51 Hz, 1H) 3.97-3.99 (m, 4H) 3.10 (quin, J=7.03 Hz, 1H) 1.36 (s, 4H) 1.34 (s, 3H). MS: MS m/z 302.1 (M++1).

Reference： [1]Patent: US2014/127156,2014,A1 .Location in patent: Page/Page column

65
[ 49633-25-2 ]
[ 549494-70-4 ]
H(CzPziPr) [ No CAS ]

Reference： [1]Organometallics,2014,vol. 33,p. 3005 - 3011

66
methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate [ No CAS ]
[ 49633-25-2 ]
methyl 4-((4,4,4-trifluoro-1-(4-(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenyl)butyl)amino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
316.2 mg	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate; In toluene; at 110℃;Inert atmosphere;	Under a nitrogen atmosphere, a mixture of methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate (racemate) (400 mg), <strong>[49633-25-2]3-isopropylpyrazole</strong> (154 mg), copper(I) iodide (212 mg), trans-N,N'-dimethylcyclohexane-1,2-diamine (0.352 mL), potassium carbonate (385 mg) and toluene (1.8 mL) was stirred at 110C overnight, water was added at room temperature, and the insoluble material was filtered off through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (316.2 mg). MS (ESI+) : [M+H]+460.2.

Reference： [1]Patent: EP2832725,2015,A1 .Location in patent: Paragraph 0351

67
[ 589-87-7 ]
[ 49633-25-2 ]
1-(4-bromo-phenyl)-3-isopropyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 100℃; for 3h;Inert atmosphere;	1-(4-Bromo-phenyl)-<strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> <strong>[49633-25-2]3-Isopropylpyrazol</strong>e (588 mg, 5.43 mmol), 1-bromo-4-iodobenzene (15.11 g, 53.4 mmol), cesium carbonate (5.22 g, 16.0 mmol), copper(I)iodide (1.02 g, 5.34 mmol) and N,N'-dimethylethylenediamine (570 uL, 5.34 mmol) are combined in dry N,N-dimethylformamide (100 mL) and heated at 100 C. for 3 hours under a nitrogen atmosphere. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (30% dichloromethane in cyclohexane) to give the title compound (Yield 1.37 g) LC (METHOD 5): tR=1.47 min; Mass spectrum (ES+): m/z=265/267 [M+H]+.
1.37 g	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 100℃; for 3h;Inert atmosphere;	Intermediate 37 1 - 4-Bromo-phenyl)-3-isopropyl-1 H-pyrazole 3- lsopropylpyrazole (588 mg, 5.43 mmol), 1 -bromo-4-iodobenzene (15.1 1 g, 53.4 mmol), cesium carbonate (5.22 g, 1 6.0 mmol), copper(l)iodide (1 .02 g, 5.34 mmol) and Nu,Nu'- dimethylethylenediamine (570 uL, 5.34 mmol) are combined in dry N,N-dimethylformamide (100 ml_) and heated at 100 C for 3 hours under a nitrogen atmosphere. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (30% dichloromethane in cyclohexane) to give the title compound (Yield 1 .37 g) LC (METHOD 5) : tR = 1 .47 min ; Mass spectrum (ES+): m/z = 265/267 [M+H]+.

Reference： [1]Patent: US2015/148347,2015,A1 .Location in patent: Paragraph 0419-0420
[2]Patent: WO2015/78802,2015,A1 .Location in patent: Page/Page column 69

68
[ 49633-25-2 ]
[ 5437-45-6 ]
benzyl 2-(3-isopropylpyrazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		[00754] Intermediate 80a: benzyl 2-(3-isopropylpyrazol-1 -yI)acetate[00755] 5-lsopropyl-1H-pyrazole (1 00mg, 0.91 mmol) and potassium carbonate (376mg, 2.72mmol) was left to stir in MeCN (3mL) for 30 mins before the addition of benzyl bromoacetate (0.21 mL, 1 .36mmol). The resultant mixture was heated to 60 C and left to stir at temperature overnight. The reaction was then quenched by addition of water (2OmL) and extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give benzyl 2-(3-isopropylpyrazol-1-yl)acetate (200mg, 0.77mmol, 85%) which was used inthe next step without further purification.1H NMR (CDCI3,400MHZ) O/ppm: 7.41-7.33 (6H, m), 6.18 (1H, d, J= 2.3Hz), 5.21 (2H, 5), 4.96 (2H, 5), 3.04 (1H, sept, J= 7.0Hz), 1.31 (3H, 5), 1.29 (3H, 5).MS Method 2: RT: 1.87 mi mlz 259.0 [M+H]

Reference： [1]Patent: WO2016/51193,2016,A1 .Location in patent: Paragraph 00753; 00754; 00755

69
[ 49633-25-2 ]
[ 1531555-49-3 ]

Reference： [1]Patent: WO2016/51193,2016,A1
[2]Patent: WO2020/95176,2020,A1

70
[ 7646-69-7 ]
[ 49633-25-2 ]
[ 21205-91-4 ]
C₂₀H₃₂BN₄^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 10194 - 10199

71
[ 598-23-2 ]
[ 18107-18-1 ]
[ 49633-25-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	at 135℃; for 1h;Microwave irradiation;	A mixture of 3-methyl-but-1-yne (0.40 g, 5.88 mmol) in trimethylsilanylmcthanediazonium (3 mL) was heated at 135 C for 1 h in a microwave reactor. The mixture was concentrated at low temperature to afford 3-isopropyl-1H-pyrazole as a yellow oil (380 mg50%).

Reference： [1]Patent: WO2017/19804,2017,A2 .Location in patent: Paragraph 0328

72
[ 49633-25-2 ]
[ 74-88-4 ]
3-isopropyl-1-methyl-1H-pyrazol-4-ylamine [ No CAS ]
C₇H₁₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-isopropyl-IH-pyrazole (380 mg, 3.45 mmol) inDMF (8 mE) were added iodomethane (2.50 g, 17.3 mmol) and K2C03 (1.40 g, 10.4 mmol). The suspension was stirred at 20 C for 16 h before it was diluted with H20 (20 mL) and extracted with Et20 (3 x20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford a mixture of 3 -isopropyl- 1-methyl- 1H-pyrazole and 5-isopropyl- 1-methyl- 1H-pyrazole as a brown solid (350 mg, 82%).; To a solution of 3-isopropyl-1-methyl-1H-pyrazole and 5-isopropyl-1-methyl-1H-pyrazole (350 mg, 2.80 mmol) from Step 2 of this example in concentrated H2S04 (2 mL) at-0 C was added KNO3 (297 mg, 2.94 mmol) portion wise. The suspension was stirred at -10C for 2 h before it was poured into ice-water and extracted with DCM (3 x50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC, eluting with petroleum ether/ethyl acetate (5:1, v/v) to afford a mixture of 3-isopropyl-1-methyl-4-nitro- 1H-pyrazole and 5- isopropyl-1-methyl-4-nitro-1H-pyrazole as a brown oil (130 mg, 27%); To a solution of 3-isopropyl-1-methyl-4-nitro-IH-pyrazole and 5-isopropyl-1- methyl-4-nitro-1H-pyrazole (150 mg, 0.88 mmol) in EtOH (10 mL) was added Pd/C (20 mg). The suspension was stirred at 20 C for 3 h under a H2 balloon. The mixture was filtered and concentrated under reduced pressure. The residue was purified by preparative TLC, eluting with DCM/MeOH (19:1, v/v) to afford 3-isopropyl-1-methyl-1H-pyrazol-4-ylamine as brown oil (55 mg, 44%).

Reference： [1]Patent: WO2017/19804,2017,A2 .Location in patent: Paragraph 0329; 0330; 0331

73
[ 49633-25-2 ]
[ 74-88-4 ]
[ 58442-49-2 ]
[ 58442-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 3-isopropyl-IH-pyrazole (380 mg, 3.45 mmol) inDMF (8 mE) were added iodomethane (2.50 g, 17.3 mmol) and K2C03 (1.40 g, 10.4 mmol). The suspension was stirred at 20 C for 16 h before it was diluted with H20 (20 mL) and extracted with Et20 (3 x20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford a mixture of 3 -isopropyl- 1-methyl- 1H-pyrazole and 5-isopropyl- 1-methyl- 1H-pyrazole as a brown solid (350 mg, 82%).

Reference： [1]Patent: WO2017/19804,2017,A2 .Location in patent: Paragraph 0329

74
[ 49633-25-2 ]
[ 74-88-4 ]
3-isopropyl-1-methyl-4-nitro-1H-pyrazole [ No CAS ]
5-isopropyl-1-methyl-4-nitro-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-isopropyl-IH-pyrazole (380 mg, 3.45 mmol) inDMF (8 mE) were added iodomethane (2.50 g, 17.3 mmol) and K2C03 (1.40 g, 10.4 mmol). The suspension was stirred at 20 C for 16 h before it was diluted with H20 (20 mL) and extracted with Et20 (3 x20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford a mixture of 3 -isopropyl- 1-methyl- 1H-pyrazole and 5-isopropyl- 1-methyl- 1H-pyrazole as a brown solid (350 mg, 82%).; To a solution of 3-isopropyl-1-methyl-1H-pyrazole and 5-isopropyl-1-methyl-1H-pyrazole (350 mg, 2.80 mmol) from Step 2 of this example in concentrated H2S04 (2 mL) at-0 C was added KNO3 (297 mg, 2.94 mmol) portion wise. The suspension was stirred at -10C for 2 h before it was poured into ice-water and extracted with DCM (3 x50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC, eluting with petroleum ether/ethyl acetate (5:1, v/v) to afford a mixture of 3-isopropyl-1-methyl-4-nitro- 1H-pyrazole and 5- isopropyl-1-methyl-4-nitro-1H-pyrazole as a brown oil (130 mg, 27%).

Reference： [1]Patent: WO2017/19804,2017,A2 .Location in patent: Paragraph 0329; 0330

75
[ 49633-25-2 ]
2-{2-fluoro-4-[2-(3-isopropyl-1-methyl-1H-pyrazol-4-ylamino)-pyrimidin-5-yl]-phenyl}-N-[5-(1-trifluoromethyl-cyclopropyl)-isoxazol-3-yl]-acetamide [ No CAS ]

Reference： [1]Patent: WO2017/19804,2017,A2

76
[ 49633-25-2 ]
(5-bromo-pyrimidin-2-yl)-(3-isopropyl-1-methyl-1H-pyrazol4-yl)-amine [ No CAS ]

Reference： [1]Patent: WO2017/19804,2017,A2

77
[ 55934-22-0 ]
[ 49633-25-2 ]
[ 1608477-31-1 ]

Yield	Reaction Conditions	Operation in experiment
14%	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 18h;	To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.54 g, 2.36 mmol) in DMF (5 ml) was added Cs2CO3 (1.54 g, 4.74 mmol) followed by <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.78 g, 7.10 mmol). The reaction mixture was heated to 80 C. for 18 h. The reaction mass was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure to get crude compound. The crude compound was silica gel chromatography to get desired compound (0.1 g, 14%) as white solid. 1H NMR (400 MHz, CDCl3): delta ppm 8.60 (d, J=2.51 Hz, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 7.26 (s, 2H) 7.16-7.22 (m, 1H) 6.35 (d, J=2.51 Hz, 1H) 3.97-3.99 (m, 4H) 3.10 (quin, J=7.03 Hz, 1H) 1.36 (s, 4H) 1.34 (s, 3H). MS: MS m/z 302.1 (M++1).

Reference： [1]Patent: US9643999,2017,B2 .Location in patent: Page/Page column 77

78
[ 49633-25-2 ]
[ 70-11-1 ]
2-(3-isopropyl-1H-pyrazol-1-yl)-1-phenylethan-1-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

79
[ 49633-25-2 ]
(2-isopropylpyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

80
[ 49633-25-2 ]
(8-fluoro-2-isopropylpyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

81
[ 49633-25-2 ]
(8-chloro-2-isopropylpyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

82
[ 49633-25-2 ]
(2-isopropyl-9-methylpyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

83
[ 49633-25-2 ]
(2-isopropyl-8,9-dimethoxypyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

84
[ 49633-25-2 ]
(2-isopropyl-[1,3]dioxolo[4,5-g]pyrazolo[5,1-a]isoquinolin-5-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

85
[ 49633-25-2 ]
(2-isopropyl-4-phenylpyrazolo[1,5-a]pyridin-7-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1973 - 1983

86
[ 49633-25-2 ]
[ 308847-51-0 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 14254 - 14268

87
[ 49633-25-2 ]
2-(3-isopropyl-1H-pyrazol-1-yl)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8797 - 8810

88
[ 49633-25-2 ]
N-(4-((6,7-dimethoxyquinazolin-4-yl)oxy)phenyl)-2-(3-isopropyl-1H-pyrazol-1-yl)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8797 - 8810

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Precautionary Statements-General
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P320
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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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.
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P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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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
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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Storage
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P401
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Disposal
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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
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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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
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
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H310	Fatal in contact with skin
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H312	Harmful in contact with skin
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H330	Fatal if inhaled
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H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H340	May cause genetic defects
H341	Suspected of causing genetic defects
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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

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[ 49633-25-2 ] Synthesis Path-Upstream 1~7

[ 49633-25-2 ] Synthesis Path-Downstream 1~88

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Pyrazoles

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