107862-65-7|5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole| Ambeed

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Quality Control of [ 107862-65-7 ] Purity: 95% SDS Specification

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Product Details of [ 107862-65-7 ]

CAS No. :	107862-65-7
Formula :	C₆H₈N₂
M.W :	108.14
SMILES Code :	C1CN2N=CC=C2C1
MDL No. :	MFCD18072560
InChI Key :	LQKUERRPRLVSLZ-UHFFFAOYSA-N
Pubchem ID :	11073365

Safety of [ 107862-65-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 107862-65-7 ]

* 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.

Downstream synthetic route of [ 107862-65-7 ]

[ 107862-65-7 ] Synthesis Path-Downstream 1~24

1
[ 100-58-3 ]
3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole [ No CAS ]
[ 107862-65-7 ]
[ 10183-74-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 1095 - 1096.

2
[ 174790-34-2 ]
[ 107862-65-7 ]

Yield	Reaction Conditions	Operation in experiment
39.6%	With potassium hydroxide; In water; isopropyl alcohol; at 90℃; for 2.0h;	To a solution of 3-(3-chloropropyl)-1H-pyrazole (500 mg, 3.5 mmol) in i-PrOH/H2O (5 mL/1 mL) was added potassium hydroxide (389 mg, 6.9 mmol) and then the reaction mixture was stirred at 90 C. for 2 hrs. The reaction mixture was cooled to ambient temperature, extracted with DCM (3×20 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (PE: EtOAc=6:1 to 2:1) to give the title compound (150 mg, 39.6% yield) as brown oil. LC-MS (ESI) found: 109 [M+1]
	With potassium hydroxide; In water; isopropyl alcohol; for 4.0h;Reflux;	To a solution of 3-(3-chloropropyl)-lH-pyrazole in isopropanol (80% solution in water, 30 mL) was added potassium hydroxide (2.0 g, 36 mmol) and then the reaction mixture was heated to reflux. After 4 hours, the reaction mixture was cooled to ambient temperature, diluted with water (15 mL), and extracted with DCM (3 x 30 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford 5,6-dihydro-4H- pyrrolo[l ,2-&]pyrazole.
	With potassium hydroxide; In water; isopropyl alcohol; for 4.0h;Reflux;	Compound 15 (0.111mol, 16.0g) was dissolved in a mixture of 2-propanol (240mL) and water (30mL) and KOH (0.122mol, 6.80g) in water (30mL) was added. The reaction mixture was heated to reflux for 4h, then the solution was concentrated and the residue was diluted by 50mL of water. This suspension was extracted with DCM (4×75mL); the combined organic extracts were dried over MgSO4, and concentrated under reduced pressure. The crude product (10.9g of a light yellow liquid) was used without further purification. 1H NMR: delta=7.49 (s, 1H, CH), 5.94 (s, 1H, CH), 4.12 (t, 3J=7.2, 2H, NCH2), 2.84-2.92 (m, 2H, =C-CH2), 2.53-2.65 (m, 2H, NCH2CH2); 13C NMR: delta=145.7 (C), 143.8 (CH), 98.7 (CH), 47.6 (CH2), 26.6 (CH2), 23.0 (CH2); GC-MS m/z (%): 108 (M+, 100), 80 (35), 52 (32); FTIR (film): 2954, 2920, 1614, 1453, 1410, 1323, 1174, 1033, 943. HRMS m/z calcdfor C6H9N2: 109.0760. Found: 109.0765.

With potassium hydroxide; In water; isopropyl alcohol; for 4.0h;Reflux;

Step 7: Potassium hydroxide (2.0 g, 36 mmol) was added to the solution of the crude 3- (3-chloro-propyl)-lH-pyrazole in z'-PrOH (80 % in water, 30 mL). The mixture was heated to reflux for 4 hr then cooled to room temperature and diluted with water (15 mL). The aqueous layer was extracted with dichloromethane (3 x 30 mL) and the organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole.

References: [1]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 0953.
[2]Tetrahedron Letters,1996,vol. 37,p. 1095 - 1096.
[3]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00248.
[4]Tetrahedron,2013,vol. 69,p. 7139 - 7146.
[5]Patent: WO2013/192125,2013,A1 .Location in patent: Page/Page column 135.

3
[ 107862-65-7 ]
3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	To a stirred solution of 5 (1.0 equiv, 4.3 g, 40.0 mmol) in DMF (50 mL) was added NBS (1.1 equiv, 7.8 g, 44.0 mmol) in portions at room temperature, and the resulting solution was stirred overnight. After concentration under vacuum, the residue was diluted with EtOAc (100 mL), washed with brine (2 × 30 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluted with PE/EtOAc (2/1) to afford 6 (6.5 g). Yield: 87% of yellow solid; ESI(+)-MS: mlz: 187.0 (M+1); 1H NMR (CDCl3, 300 MHz) delta: 7.43 (s, 1 H), 4.16 (t, J = 7.2 Hz, 2 H), 2.85 (t, J = 7.2 Hz, 2 H), 2.64-2.57 (m, 2 H).
46.4%	With bromine; sodium acetate; acetic acid; at 0℃; for 0.166667h;	To a solution of <strong>[107862-65-7]5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole</strong> (150 mg, 1.39 mmol) and sodium acetate (114 mg, 1.39 mmol) in acetic acid (1.5 mL) at 0 C. was added bromine (197.5 mg, 1.25 mmol). After 10 minutes, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with 5% Na2S2O4, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (PE: EtOAc=6:1 to 4:1) to give the title compound (120 mg, yield 46.4%) as white solid.
	With bromine; sodium acetate; In acetic acid; at 0℃; for 0.166667h;	To a solution of 5,6-dihydro-4H-pyrrolo[l ,2-Z?]pyrazole (47.2 g, 437 mmol) and sodium acetate (36.2 g, 440 mmol) in acetic acid (750 mL) at 0C was added bromine (22.4 mL, 435 mmol). After 10 minutes, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (5 x 200 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[l,2-6]pyrazole.

1.43 g	With N-Bromosuccinimide; In chloroform; at 20℃; for 0.08333330000000001h;Inert atmosphere;	The bicyclic compound 16 (9mmol, 973mg) was dissolved in dry CHCl3 (40mL) and NBS (10mmol, 1.73g) was added. The bright red reaction mixture was stirred for 5min at room temperature. The mixture was diluted in CHCl3 (20mL), washed with water (3×50mL), dried over MgSO4, and concentrated in vacuo. The crude brown solid was dissolved in Et2O and filtered through a thin layer of silica gel. Evaporation of the solvent afforded a light yellow crystalline product (1.43g) in 77% yield (MP 82.6-84.0C) from 14. It became dark after standing at room temperature and at a lower temperature. Mp: 82.6-84.0C; 1H NMR: delta=7.43 (s, 1H, CH), 4.16 (t, 3J=7.3, 2H, NCH2), 2.82-2.87 (m, 2H, =C-CH2), 2.58-2.66 (m, 2H, NCH2CH2); 13C NMR: delta=144.8 (C), 143.9 (CH), 86.7 (C-Br), 49.0 (CH2), 26.2 (CH2), 22.6 (CH2); GC-MS m/z (%): 188 (M++1, 64), 186 (63), 107 (93), 80 (49), 51 (100); FTIR (KCl): 2962, 2922, 2854, 1706, 1641, 1452, 1318, 1226, 1156, 1013, 986. HRMS m/z calcdfor C6H8N2Br: 186.9871. Found: 186.9873.
73.5 g	With bromine; sodium acetate; acetic acid; at 0℃; for 0.166667h;	Step 8: Bromine (22.4 mL, 435 mmol) was added to a solution of 5,6-dihydro-4H- pyrrolo[l,2-b]pyrazole 8 (47.2 g, 437 mmol) and NaOAc (36.2 g, 440 mmol) in AcOH (750 mL) o drop wise at 0 C. The mixture was stirred at the same temperature for 10 minutes then neutralized by the addition of aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (5 x 200 mL) and the organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole (73.5 g).

References: [1]Heterocycles,2017,vol. 94,p. 1923 - 1930.
[2]Tetrahedron Letters,1996,vol. 37,p. 1095 - 1096.
[3]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 0954.
[4]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00249.
[5]Tetrahedron,2013,vol. 69,p. 7139 - 7146.
[6]Patent: WO2013/192125,2013,A1 .Location in patent: Page/Page column 135.

4
[ 107862-65-7 ]
[ 10183-74-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 1095 - 1096.
[2]Tetrahedron,2013,vol. 69,p. 7139 - 7146.

5
1-bromo-6-chlorohexan-3-one [ No CAS ]
[ 107862-65-7 ]

References: [1]Tetrahedron,2013,vol. 69,p. 7139 - 7146.
[2]Patent: WO2013/192125,2013,A1 .
[3]Patent: WO2017/35353,2017,A1 .
[4]Patent: WO2013/52394,2013,A1 .

6
[ 76328-94-4 ]
[ 107862-65-7 ]

References: [1]Tetrahedron,2013,vol. 69,p. 7139 - 7146.
[2]Patent: WO2013/192125,2013,A1 .
[3]Patent: WO2017/35353,2017,A1 .
[4]Patent: WO2013/52394,2013,A1 .

7
[ 1429913-29-0 ]
[ 107862-65-7 ]

References: [1]Patent: WO2013/192125,2013,A1 .
[2]Patent: WO2017/35353,2017,A1 .
[3]Patent: WO2013/52394,2013,A1 .

8
[ 107862-65-7 ]
[ 1314138-13-0 ]

References: [1]Patent: WO2013/192125,2013,A1 .
[2]Patent: WO2013/52394,2013,A1 .

9
[ 107862-65-7 ]
[ 1426535-54-7 ]

References: [1]Tetrahedron,2013,vol. 69,p. 7139 - 7146.

10
[ 107862-65-7 ]
[ 1447997-29-6 ]

References: [1]Tetrahedron,2013,vol. 69,p. 7139 - 7146.

11
[ 107862-65-7 ]
[ 1447997-30-9 ]

References: [1]Tetrahedron,2013,vol. 69,p. 7139 - 7146.

12
[ 107862-65-7 ]
tert-butyl 2-(3-acetyl-5-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-1H-indazol-1-yl)acetate [ No CAS ]