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[ CAS No. 635702-60-2 ] {[proInfo.proName]}

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Chemical Structure| 635702-60-2
Chemical Structure| 635702-60-2
Structure of 635702-60-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 635702-60-2 ]

CAS No. :635702-60-2 MDL No. :MFCD09258896
Formula : C9H12ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :DYTQJZDNKWQSLS-UHFFFAOYSA-N
M.W : 197.67 Pubchem ID :46864001
Synonyms :

Calculated chemistry of [ 635702-60-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.33
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.27
Log Po/w (MLOGP) : 1.46
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.252 mg/ml ; 0.00127 mol/l
Class : Soluble
Log S (Ali) : -2.64
Solubility : 0.452 mg/ml ; 0.00229 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.64 mg/ml ; 0.00324 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 635702-60-2 ]

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 [ 635702-60-2 ]

* 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 [ 635702-60-2 ]
  • Downstream synthetic route of [ 635702-60-2 ]

[ 635702-60-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 444731-73-1 ]
  • [ 635702-60-2 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; To a stirred solution of 2, [3-DIMETHYL-6-NITRO-2H-INDAZOLE] (1.13 g) in 2- methoxyethyl ether (12 [ML),] at [0] [C,] was added a solution of 4.48 g of tin [(LL)] chloride in 8.9 ml of concentrated HCI dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 [percent),] the HCI salt 2,3- [DIMETHYL-2H-INDAZOL-6-AMINE.APOS;H] NMR (300 MHz, [DMSO-D6)] 8 7. [77] (d, [J =] 8.9 [HZ,] [1 H),] 7.18 (s, [1 H),] 7.88 (m, [1 H),] 4.04 (s, 3H), 2.61 (s, 3H). MS [(ES+,] m/z) 162 (M+H).
95% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; To a stirred solution of 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) in 2- methoxyethyl ether (12 ml), at 0 9C, was added a solution of 4.48 g of tin(ll) chloride in 8.9 ml of concentrated HCI dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 percent), the HCI salt 2,3-dimethyl-2H-indazol- 6-amine. 1H NMR (300 MHz, DMSO-d6) δ 7.77 (d, J = 8.9 Hz, 1 H), 7.18 (s, 1H), 7.88 (m, 1 H), 4.04 (s, 3H), 2.61 (s, 3H). MS (ES+, m/z) 162 (M+H).
95% With tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; To a stirred solution of 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) in 2- methoxyethyl ether (12 ml), at 0 9C, was added a solution of 4.48 g of tin(ll) chloride in 8.9 ml of concentrated HCI dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 percent), the HCI salt 2,3-dimethyl-2H-indazol- 6-amine. 1H NMR (300 MHz, DMSO-d6) δ 7.77 (d, J = 8.9 Hz, 1 H), 7.18 (s, 1 H), 7.88 (m, 1 H), 4.04 (s, 3H), 2.61 (s, 3H). MS (ES+, m/z) 162 (M+H).
95% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; Inert atmosphere; Cooling with ice Intermediate Example 11
Preparation of 2,3-dimethyl-2H-indazol-6-amine
To a stirred solution of 18.5 g (0.11 mol) of 3-methyl-6-nitro-1H-indazole in 350 ml acetone, at room temperature, was added 20 g (0.14 mol) of trimethyloxonium tetraflouroborate.
After the solution was allowed to stir under argon for 3 hours, the solvent was removed under reduced pressure.
To the resulting solid was added saturated aqueous NaHCO3 (600 ml) and a 4:1 mixture of chloroform-isopropanol (200 ml), and the mixture was agitated and the layers were separated.
The aqueous phase was washed with additional chloroform: isopropanol (4 x 200 ml) and the combined organic phase was dried (Na2SO4).
Filtration and removal of solvent gave a tan solid.
The solid was washed with ether (200 ml) to afford 2,3-dimethyl-6-nitro-2H-indazole as a yellow solid (15.85 g, 73 percent).
1H NMR (300 MHz, d6DMSO) δ 8.51 (s, 1H), 7.94 (d, J = 9.1 Hz, 1H), 7.73 (d, J = 8.9 Hz, 1H), 4.14 (s, 3H), 2.67 (s, 3H). MS (ES+, m/z) 192 (M+H).; To a stirred solution of 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) in 2-methoxyethyl ether (12 ml), at 0 °C, was added a solution of 4.48 g of tin(II) chloride in 8.9 ml of concentrated HCl dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 percent), the HCl salt 2,3-dimethyl-2H-indazol-6-amine. 1H NMR (300 MHz, d6DMSO) δ 7.77 (d, J = 8.9 Hz, 1H), 7.18 (s, 1H), 7.88 (m, 1H), 4.04 (s, 3H), 2.61 (s, 3H). MS (ES+, m/z) 162 (M+H).
95% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; Intermediate Example 2
Preparation of 2,3-dimethyl-6-amino-2H-indazole
Procedure 1:
To a stirred solution of 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) in 2-methoxyethyl ether (12 ml), at 0° C., was added a solution of 4.48 g of tin(II) chloride in 8.9 ml of concentrated HCl dropwise over 5 min.
After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min.
Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation.
The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95percent), the HCl salt 2,3-dimethyl-2H-indazol-6-amine. 1H NMR (300 MHz, DMSO-d6) δ 7.77 (d, J=8.9 Hz, 1H), 7.18 (s, 1H), 7.88 (m, 1H), 4.04 (s, 3H), 2.61 (s, 3H). MS (ES+, m/z) 162 (M+H).
95% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; Intermediate Example 2 Preparation of 2,3-dimethyl-6-amino-2H-indazole Procedure 1: To a stirred solution of 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) in 2- methoxyethyl ether (12 ml), at 0 °C, was added a solution of 4.48 g of tin(II) chloride in 8.9 ml of concentrated HCI dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 percent), the HCI salt 2,3-dimethyl-2H-indazol-6-amine.
95% With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0℃; for 0.583333 h; To a stirred solution of 2,3-dimethyl-6-nitro-2/-/-indazole (1.13 g) in 2- methoxyethyl ether (12 ml), at 0 0C, was added a solution of 4.48 g of tin(ll) chloride in 8.9 ml of concentrated HCI dropwise over 5 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 40 ml of diethyl ether was added to reaction, resulting in precipitate formation. The resulting precipitate was isolated by filtration and washed with diethyl ether, and afforded a yellow solid (1.1 g, 95 percent), the HCI salt 2,3-dimethyl-2H-indazol-6- amine. 1H NMR (300 MHz, DMSOd6) δ 7.77 (d, J = 8.9 Hz, 1 H), 7.18 (s, 1 H), 7.88 (m, 1 H), 4.04 (s, 3H), 2.61 (s, 3H). MS (ES+, m/z) 162 (M+H).

Reference: [1] Patent: WO2003/106416, 2003, A2, . Location in patent: Page 42-43
[2] Patent: WO2007/64753, 2007, A2, . Location in patent: Page/Page column 27
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4632 - 4640
[4] Patent: WO2006/20564, 2006, A1, . Location in patent: Page/Page column 14
[5] Patent: EP2311825, 2015, B1, . Location in patent: Paragraph 0178 - 0180
[6] Patent: US2008/293691, 2008, A1, . Location in patent: Page/Page column 8-9
[7] Patent: WO2005/105094, 2005, A2, . Location in patent: Page/Page column 29-30
[8] Patent: WO2007/143483, 2007, A2, . Location in patent: Page/Page column 30
  • 2
  • [ 6494-19-5 ]
  • [ 635702-60-2 ]
Reference: [1] Patent: US2008/293691, 2008, A1,
[2] Patent: US2008/293691, 2008, A1,
[3] Patent: WO2005/105094, 2005, A2,
[4] Patent: WO2007/143483, 2007, A2,
[5] Patent: US2008/293691, 2008, A1,
[6] Patent: WO2005/105094, 2005, A2,
[7] Patent: WO2007/143483, 2007, A2,
[8] Patent: WO2005/105094, 2005, A2,
[9] Patent: WO2007/143483, 2007, A2,
  • 3
  • [ 635702-59-9 ]
  • [ 635702-60-2 ]
Reference: [1] Patent: US2008/293691, 2008, A1,
[2] Patent: WO2005/105094, 2005, A2,
[3] Patent: WO2007/143483, 2007, A2,
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