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Chemical Structure| 114153-25-2 Chemical Structure| 114153-25-2

Structure of 114153-25-2

Chemical Structure| 114153-25-2

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Product Details of [ 114153-25-2 ]

CAS No. :114153-25-2
Formula : C7H10N2O
M.W : 138.17
SMILES Code : O=C(NCC1CC1)CC#N

Safety of [ 114153-25-2 ]

Application In Synthesis of [ 114153-25-2 ]

* 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.

  • Downstream synthetic route of [ 114153-25-2 ]

[ 114153-25-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 114153-25-2 ]
  • [ 17983-30-1 ]
  • [ 4023-34-1 ]
  • 5-cyano-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide [ No CAS ]
  • 7-cyano-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9%; 0.8% To 3-oxocyclohexane-l-carbonitrile [17983-30-1] (63 mg, 0.49 mmol) and 2-cyano-N- (cyclopropylmethyl)acetamide [114153-25-2] (79 mg, 0.55 mmol) in THF (1 mL) was added ammonium acetate (52 mg, 0.675 mmol) and acetic acid (30 m). The reaction mixture was stirred at 70 C for 3 h. To the reaction mixture was added sulphur [7704-34-9] (26 mg, 0.81 mmol), EtOH (3 mL) and triethylamine (210 pL, 1.49 mmol) and the mixture was warmed at 65 C overnight and the mixture was concentrated in vacuo. To the residue was added EtOAc (5 mL) and 10% potassium bisulfate (2 mL), the organic layer was separated and washed with saturated sodium hydrogen carbonate solution followed by brine. The organic phase was separated, dried (Na2S04), filtered and concentrated in vacuo to yield a crude brown oil. To the residue was added DCM (2.5 mL) and DIPEA (130 pL, 0.75 mmol) and the mixture was cooled to 0 C in an ice-bath and a solution of (4293) cyclopropanecarbonyl chloride [4023-34-1] (75 mg, 0.70 mmol) in DCM (0.5 mL) was added. The reaction mixture was stirred at r.t. for 4 h before addition of saturated sodium hydrogen carbonate solution. The organic phase was separated with a phase separation cartridge and the aqueous was further extracted with DCM (2 mL). The combined organic layers were concentrated in vacuo to yield the crude products which were purified by preparative HPLC (basic), to afford title compound example 64 (15 mg, 9%). LCMS [M+H]+ 344.10, RT 4.11 minutes, (Methodl3). Preparative HPLC purification (acidic) of impure fractions from the initial purification (basic) afforded title compound example 65 (1.4 mg, 0.8%). LCMS [M+H]+ 344.10, [M+Na]+ 366.13, RT 4.60 minutes, 100.0% purity (Method 21). LCMS [M+H]+ 344.10, [M+Na]+ 366.08, [M-H] 342.06, RT 4.30 minutes, 97.08% purity (Method 13).
  • 2
  • [ 114153-25-2 ]
  • [ 17983-30-1 ]
  • C14H17N3OS [ No CAS ]
  • C14H17N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
To 3-oxocyclohexane-l-carbonitrile [17983-30-1] (63 mg, 0.49 mmol) and 2-cyano-N- (cyclopropylmethyl)acetamide [114153-25-2] (79 mg, 0.55 mmol) in THF (1 mL) was added ammonium acetate (52 mg, 0.675 mmol) and acetic acid (30 m). The reaction mixture was stirred at 70 C for 3 h. To the reaction mixture was added sulphur [7704-34-9] (26 mg, 0.81 mmol), EtOH (3 mL) and triethylamine (210 pL, 1.49 mmol) and the mixture was warmed at 65 C overnight and the mixture was concentrated in vacuo. To the residue was added EtOAc (5 mL) and 10% potassium bisulfate (2 mL), the organic layer was separated and washed with saturated sodium hydrogen carbonate solution followed by brine. The organic phase was separated, dried (Na2S04), filtered and concentrated in vacuo to yield a crude brown oil. To the residue was added DCM (2.5 mL) and DIPEA (130 pL, 0.75 mmol) and the mixture was cooled to 0 C in an ice-bath and a solution of (4293) cyclopropanecarbonyl chloride [4023-34-1] (75 mg, 0.70 mmol) in DCM (0.5 mL) was added. The reaction mixture was stirred at r.t. for 4 h before addition of saturated sodium hydrogen carbonate solution. The organic phase was separated with a phase separation cartridge and the aqueous was further extracted with DCM (2 mL). The combined organic layers were concentrated in vacuo to yield the crude products which were purified by preparative HPLC (basic), to afford title compound example 64 (15 mg, 9%). LCMS [M+H]+ 344.10, RT 4.11 minutes, (Methodl3). Preparative HPLC purification (acidic) of impure fractions from the initial purification (basic) afforded title compound example 65 (1.4 mg, 0.8%). LCMS [M+H]+ 344.10, [M+Na]+ 366.13, RT 4.60 minutes, 100.0% purity (Method 21). LCMS [M+H]+ 344.10, [M+Na]+ 366.08, [M-H] 342.06, RT 4.30 minutes, 97.08% purity (Method 13).
 

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