146950-68-7|N4-Cyclopropylpyridine-3,4-diamine| Ambeed

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Quality Control of [ 146950-68-7 ] Purity: 98% SDS Specification

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Product Details of [ 146950-68-7 ]

CAS No. :	146950-68-7
Formula :	C₈H₁₁N₃
M.W :	149.19
SMILES Code :	NC1=C(NC2CC2)C=CN=C1
MDL No. :	MFCD09954764
InChI Key :	VPGWOWXXDKITFM-UHFFFAOYSA-N
Pubchem ID :	19102553

Safety of [ 146950-68-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 146950-68-7 ]

* 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 [ 146950-68-7 ]

[ 146950-68-7 ] Synthesis Path-Downstream 1~35

1
[ 380605-28-7 ]
[ 146950-68-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr;	Step 2: Synthesis of N'-cyclopropylpyridine-S^-diamine 5-c5- b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10%) Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with MTBE to afford compound 5-c as a yellow powder (133 g, 95%).
95%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr;	Intermediate 7-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10 % Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl terbutyl ether to afford the title compound 7-c (133 g, 95%) as a yellow powder.
95%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr;	Step 2: Synthesis of N4-cyclopropylpyridine-3,4-diamine(5-c)A mixture of the intermediate 5-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10% Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with MTBE to afford compound 5-c as a yellow powder (133 g, 95%).

95%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr;	Intermediate 10-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10 % Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl tert-butyl ether to afford the title compound 10-c as a yellow powder (133 g, 95%).
95%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 2585.81 Torr;	Intermediate 7-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20 C. with wet 10% Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl terbutyl ether to afford the title compound 7-c (133 g, 95%) as a yellow powder.
90.6%	With hydrogen;palladium 10% on activated carbon; In ethanol; water; at 20℃; under 2585.81 Torr; for 16.0h;	The synthesis of l-(cyclopropyl)-l,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (fragment CI) was done as shown in scheme 7.g 7 fragment C1; Scheme 7A round-bottom flask was charged with 3-nitro-4-chloropyridine (600 g, 3.8 mol), absolute EtOH (3L), diisopropylethylamine (DIPEA) (1320 mL, 7.6 mol) and cyclopropyl amine (432g, 7.6 mol). The resulting solution was refluxed for lOh. The reaction was cooled to 0C, and the solid was collected by filtration. The filter cake was washed with cold ethanol (2x500 mL) to give compound 6. The mother liquor was concentrated and partitioned between water (1000 mL) and ethyl acetate (1000 mL). The aqueous layer was extracted with ethyl acetate (2x500mL), dried over MgS04, filtered, and concentrated to give a second batch of product (total: 650 g, 96%). A suspension of compound 6 (650g, 3.65mol) and 10% Pd/C (50% water; 163 g) in EtOH (7 L) was hydrogenated at 50 psi H2 for 16 h at room temperature. The suspension was filtered through Celite and concentrated. The residue was dried in vacuo to provide compound 7 (490 g, 90.6%). To a solution of compound 7 (490 g, 3.29 mol) in CH3CN (4 L) at 0C was added carbonyldiimidazole (CDI) (559 g, 3.45 mol, 1.05eq.), and the resulting mixture was warmed to room temperature and stirred for 16 h at room temperature. The precipitate was collected by filtration and the solid was washed with cold CH3CN (2 X 1000 mL). The solid was dried in vacuo to give fragment CI . (450 g, 78.2%). m/z = 176 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.84 - 0.91 (m, 2 H), 0.98 - 1.06 (m, 2 H), 2.89 (tt, J=7.0, 3.5 Hz, 1 H), 7.18 (d, J=5.5 Hz, 1 H), 8.16 (s, 1 H), 8.19 (d, J=5.5 Hz, 1 H), 10.98 (br. s., 1 H).
	With palladium 10% on activated carbon; hydrogen; In ethanol; under 2585.81 Torr; for 2.0h;	A solution of intermediate 10a3 (3.8 g, 21 mmol) and Pd/C 10% (760 mg) in EtOH (32 mL) is stirred under hydrogen atmosphere at 50 psi for 2 h. The catalyst is filtrated through Celite. The filtrate is evaporated under reduced pressure to afford intermediate 10a4.
	With palladium 10% on activated carbon; hydrogen; In ethanol; at 30℃; under 2585.81 Torr;	To a solution of N-cyclopropyl-3-nitropyridin-4-amine (100 g, 0.560 mol) in EtOH (800 mL) was added 10% Pd/C (8 g). The mixture was stirred under 50 psi of H2 at 30 C overnight. The catalyst was filtered, and the filtrate was concentrated to afford N4-cyclopropylpyridine-3,4- diamine. 1H NMR (400 MHz, DMSO- d6): 57.70- 7.58 (m, 2 H), 6.60 (d, J= 7.2 Hz, 1H), 5.85 (s, 1 H), 4.49 (s, 2 H), 2.43- 2.41 (m, 1H), 0.71- 0.68 (m, 2 H), 0.40- 0.38 (m, 2 H). MS (El) m/z: 150 [M+H]+.

References: [1]Organic Process Research and Development,2004,vol. 8,p. 903 - 908.
[2]Patent: WO2012/80451,2012,A1 .Location in patent: Page/Page column 20.
[3]Patent: WO2012/80447,2012,A1 .Location in patent: Page/Page column 19.
[4]Patent: WO2012/80450,2012,A1 .Location in patent: Page/Page column 19.
[5]Patent: WO2012/80449,2012,A1 .Location in patent: Page/Page column 22; 23.
[6]Patent: US2013/267555,2013,A1 .Location in patent: Paragraph 0092; 0097-0098.
[7]Patent: WO2012/80446,2012,A1 .Location in patent: Page/Page column 18.
[8]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406.
[9]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 827 - 833.
[10]Patent: WO2015/65338,2015,A1 .Location in patent: Page/Page column 49.
[11]Patent: CN103860538,2016,B .Location in patent: Paragraph 0055; 0059; 0060.
[12]Patent: WO2020/247298,2020,A2 .Location in patent: Page/Page column 53-55.

2
[ 146950-68-7 ]
[ 105-56-6 ]
(1-cyclopropyl-1<i>H</i>-imidazo[4,5-<i>c</i>]pyridin-2-yl)-acetonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406.

3
[ 146950-68-7 ]
SB-736302 [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406.

4
N-Cyclopropyl-pyridine-3,4-diamine [ No CAS ]
[ 146950-68-7 ]

Yield	Reaction Conditions	Operation in experiment
		N4-Cyclopropyl-pyridine-3,4-diamine N-Cyclopropyl-pyridine-3,4-diamine was prepared by the same procedure as 1-isopropyl-1,3-dihydro-benzoimidazol-2-one and was used as crude without purification.

References: [1]Patent: US2003/207868,2003,A1 .

6
[ 146950-68-7 ]
[ 1383079-92-2 ]

References: [1]Patent: WO2012/80451,2012,A1 .

7
[ 146950-68-7 ]
[ 1383079-77-3 ]

References: [1]Patent: WO2012/80451,2012,A1 .

8
[ 146950-68-7 ]
[ 1383080-49-6 ]

References: [1]Patent: WO2012/80451,2012,A1 .

9
[ 146950-68-7 ]
[ 1383079-62-6 ]

References: [1]Patent: WO2012/80451,2012,A1 .

10
[ 146950-68-7 ]
[ 1383080-78-1 ]

References: [1]Patent: WO2012/80451,2012,A1 .

11
[ 146950-68-7 ]
[ 1383079-56-8 ]

References: [1]Patent: WO2012/80451,2012,A1 .

12
[ 146950-68-7 ]
[ 530-62-1 ]
[ 380605-29-8 ]

Yield	Reaction Conditions	Operation in experiment
78.2%	In acetonitrile; at 0 - 20℃; for 16.0h;	The synthesis of l-(cyclopropyl)-l,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (fragment CI) was done as shown in scheme 7.g 7 fragment C1; Scheme 7A round-bottom flask was charged with 3-nitro-4-chloropyridine (600 g, 3.8 mol), absolute EtOH (3L), diisopropylethylamine (DIPEA) (1320 mL, 7.6 mol) and cyclopropyl amine (432g, 7.6 mol). The resulting solution was refluxed for lOh. The reaction was cooled to 0C, and the solid was collected by filtration. The filter cake was washed with cold ethanol (2x500 mL) to give compound 6. The mother liquor was concentrated and partitioned between water (1000 mL) and ethyl acetate (1000 mL). The aqueous layer was extracted with ethyl acetate (2x500mL), dried over MgS04, filtered, and concentrated to give a second batch of product (total: 650 g, 96%). A suspension of compound 6 (650g, 3.65mol) and 10% Pd/C (50% water; 163 g) in EtOH (7 L) was hydrogenated at 50 psi H2 for 16 h at room temperature. The suspension was filtered through Celite and concentrated. The residue was dried in vacuo to provide compound 7 (490 g, 90.6%). To a solution of compound 7 (490 g, 3.29 mol) in CH3CN (4 L) at 0C was added carbonyldiimidazole (CDI) (559 g, 3.45 mol, 1.05eq.), and the resulting mixture was warmed to room temperature and stirred for 16 h at room temperature. The precipitate was collected by filtration and the solid was washed with cold CH3CN (2 X 1000 mL). The solid was dried in vacuo to give fragment CI . (450 g, 78.2%). m/z = 176 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.84 - 0.91 (m, 2 H), 0.98 - 1.06 (m, 2 H), 2.89 (tt, J=7.0, 3.5 Hz, 1 H), 7.18 (d, J=5.5 Hz, 1 H), 8.16 (s, 1 H), 8.19 (d, J=5.5 Hz, 1 H), 10.98 (br. s., 1 H).
65%	In acetonitrile; at 0 - 20℃; for 1.0h;	Step 3: Synthesis of l-cyclopropyl-lH-imidazo[4,5-c]pyridin-2(3H)-one 5-dCDI (CAS 530-62-1) (151.8 g, 936 mmol) was added to a solution of 5-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0C. The reaction was allowed to warm up to room temperature and stirred for 1 hour. The solid was collected by filtration and was washed with CH3CN (200 mL) to afford compound 5-d as a white powder (101 g, 65%).
65%	In acetonitrile; at 0 - 10℃; for 1.0h;	Carbonyldiimidazole (151.8 g, 936 mmol) was added to a solution of intermediate 7-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0C. The reaction was allowed to warm to 10C and stirred for lh. The solid was collected by filtration and was washed with CH3CN (200 ml) to afford the title compound 7-d (101 g, 65%) as a white powder.

65%	In acetonitrile; at 0 - 10℃; for 1.0h;	Step 3: Synthesis of l-cyclopropyl-lH-imidazo[4,5-c]pyridin-2(3H)-one (5-d)CDI (CAS 530-62-1) (151.8 g, 936 mmol) was added to a solution of the intermediate 5-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0C. The reaction was allowed to warm to 10C and stirred for 1 hour. The solid was collected by filtration, then washed with CH3CN (200 mL) to afford compound 5-d as a white powder (101 g, 65%).
65%	In acetonitrile; at 10℃; for 1.0h;	Carbonyldiimidazole (151.8 g, 936 mmol) was added to a solution of intermediate 10-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0C. The reaction mixture was allowed to warm to 10C and stirred for lh. The solid was collected by filtration and was washed with CH3CN (200 mL) to afford the title compound 10-d as a white powder
65%	In acetonitrile; at 0 - 10℃; for 1.0h;	Carbonyldiimidazole (151.8 g, 936 mmol) was added to a solution of intermediate 7-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0 C. The reaction was allowed to warm to 10 C. and stirred for 1 h. The solid was collected by filtration and was washed with CH3CN (200 ml) to afford the title compound 7-d (101 g, 65%) as a white powder.
	In acetonitrile; at 0 - 20℃; for 1.0h;	To a solution of intermediate 10a4 (2 g, 13.4 mmol) in ACN (40 mL) at 0QC, is added carbonyldiimidazole (2.2 g, 13.4 mmol). The mixture is stirred at RT for 1 h. The precipitate is collected by filtration to afford intermediate 3a1-3.
	In acetonitrile; at 0 - 25℃; for 1.0h;	To a solution of N-4-cyclopropylpyridine-3, 4-diamine (75.0 g, 0.503 mol) in CCN (1 L) at 0 C, CDI (100 g, 0.617 mol) was added slowly, and the resulting mixture was warmed to 25 C over 1 h. The precipitate was collected by filtration and dried in vacuo to give 1 -cyclopropyl- 1,3- dihydro-2H-imidazo[4,5-c]pyridin-2-one. 1HNMR (400 MHz, DMSO- de): 510.90 (s, 1 H), 8.20- 8.10 (m, 2 H), 7.17 (d, J= 8.0 Hz, 1 H), 2.90- 2.87 (m, 1 H), 1.01- 0.99 (m, 2 H), 0.86- 0.84 (m, 2 H). MS (El) m/z: 176 [M+H]+.

References: [1]Patent: WO2012/80446,2012,A1 .Location in patent: Page/Page column 18.
[2]Organic Process Research and Development,2004,vol. 8,p. 903 - 908.
[3]Patent: WO2012/80451,2012,A1 .Location in patent: Page/Page column 21.
[4]Patent: WO2012/80447,2012,A1 .Location in patent: Page/Page column 19.
[5]Patent: WO2012/80450,2012,A1 .Location in patent: Page/Page column 19.
[6]Patent: WO2012/80449,2012,A1 .Location in patent: Page/Page column 22; 23.
[7]Patent: US2013/267555,2013,A1 .Location in patent: Paragraph 0092; 0098-0099.
[8]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 827 - 833.
[9]Patent: WO2015/65338,2015,A1 .Location in patent: Page/Page column 49.
[10]Angewandte Chemie - International Edition,2020,vol. 59,p. 7256 - 7260.
Angew. Chem.,2020,vol. 132,p. 7323 - 7327,5.
[11]Patent: WO2020/247298,2020,A2 .Location in patent: Page/Page column 53-55.

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[ 31872-62-5 ]
[ 146950-68-7 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 827 - 833.
[3]Patent: US2013/267555,2013,A1 .
[4]Organic Process Research and Development,2004,vol. 8,p. 903 - 908.
[5]Patent: WO2015/65338,2015,A1 .
[6]Patent: CN103860538,2016,B .

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[ 146950-68-7 ]
[ 1383450-29-0 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383451-41-9 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383450-31-4 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383450-30-3 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383451-33-9 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383450-38-1 ]

References: [1]Patent: WO2012/80447,2012,A1 .
[2]Patent: US2013/267555,2013,A1 .

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[ 146950-68-7 ]
[ 1383422-75-0 ]

References: [1]Patent: WO2012/80446,2012,A1 .

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[ 146950-68-7 ]
[ 1383423-23-1 ]

References: [1]Patent: WO2012/80446,2012,A1 .

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[ 13091-23-1 ]
[ 146950-68-7 ]

References: [1]Patent: WO2012/80446,2012,A1 .

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[ 146950-68-7 ]
[ 1383252-79-6 ]

References: [1]Patent: WO2012/80450,2012,A1 .

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[ 146950-68-7 ]
[ 1383252-27-4 ]

References: [1]Patent: WO2012/80450,2012,A1 .

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[ 1383252-42-3 ]

References: [1]Patent: WO2012/80450,2012,A1 .

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[ 146950-68-7 ]
[ 1383050-29-0 ]