Alternatived Products of [ 1262397-26-1 ]
Product Details of [ 1262397-26-1 ]
CAS No. : | 1262397-26-1 |
MDL No. : | MFCD25541989 |
Formula : |
C12H22N2O2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
226.32
|
Pubchem ID : | - |
Synonyms : |
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Safety of [ 1262397-26-1 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1262397-26-1 ]
* 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 [ 1262397-26-1 ]
- 1
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[ 4472-44-0 ]
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[ 1262397-26-1 ]
-
[ 1262397-28-3 ]
Yield | Reaction Conditions | Operation in experiment |
41% |
With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 120℃; for 1h;Microwave irradiation; |
Example 40: Preparation of intermediate 67: (SHert-butyl 6-(((4,6- dimethylpyrimidin-2-yl)amino)methyl)-5-azaspiror2.41heptane-5-carboxvlateIn a microwave vial (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5- carboxylate (Intermediate 66, 61 mg, 0.27 mmol) and 2-chloro-4,6- dimerhylpyrimidine (61 mg, 0.43 mmol) were dissolved in 1 ml of isopropyl alcohol.DIPEA (0.1 ml, 0.57 mmol) was added and the vial was sealed and heated to120 C in two cycles of 30 minutes each by microwave irradiation.The solvent was then removed and the residue purified by flash chromatography on a 10g silica cartridge, eluting with a step gradient: cyclohexane/AcOEt in 2 column volumes, then linear gradient to 65/35 in 16 column volumes and finally isocratic 65/35 in 3 column volumes.Removal of the solvent yielded 37 mg of (S)-tert-butyl 6-(((4,6-dimethylpyrimidin-2- yl)amino)methyl)-5-azaspiro[2.4]heptane-5-carboxylate as a clear crust (yield 41 percent). MS (ESI) m/z 333 [M+H]+; 355 [M+Na]+1HNMR(CDCI3) d ppm 6.30-6.32 (m,1 H) 5.37-5.72 (m, 1 H) 4.1 1 -4.20 (m, 1 H) 3.60- 3.85 (m, 2H) 3.44-3.58 (m, 1 H) 3.09-3.12 (m, 1 H) 2.30 (s, 6H) 2.14-2.20 (m, 1 H) 1.50 (s, 9H) 0.85-0.95 (m, 1 H) 0.50-0.76 (m, 4H) |
- 2
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[ 22536-67-0 ]
-
[ 1262397-26-1 ]
-
[ 1262397-31-8 ]
Yield | Reaction Conditions | Operation in experiment |
61% |
With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 120℃; for 0.333333h;Microwave irradiation; |
Example 41 : Preparation of intermediate 68: (SHert-butyl 6-(((5-chloropyrimidin-2- yl)amino)methyl)-5-azaspiro[2.4]heptane-5-carboxylateIn a microwave vial (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5- carboxylate (Intermediate 66, 66 mg, 0.29 mmol) and <strong>[22536-67-0]2,5-dichloropyrimidine</strong> (65 mg, 0.44) were dissolved in 1 ml of isopropyl alcohol. DIPEA (100 ul, 0.58 mmol) was added; the vial was sealed and heated to 120 C for 20 minutes by microwave irradiation.The solvent was then removed and the residue purified by flash chromatography on a 10g silica cartridge, eluting with a step gradient: cyclohexane/AcOEt in 2 column volumes, then linear gradient to 80/20 in 10 column volumes and finally isocratic 80/20 in 2 column volumes.Removal of the solvent yielded 60 mg of (S)-tert-butyl 6-(((5-chloropyrimidin-2- yl)amino)methyl)-5-azaspiro[2.4]heptane-5-carboxylate as a white solid (yield 61 %).MS (ESI) m/z 339-341 (Cl pattern) [M+H]+; 361 -363 [M+Na]+1HNMR(CDCI3) d ppm 8.21 (s,2H) 5.62-6.5 (m, 1 H) 4.20-4.30 (m, 1 H) 3.53-3.62(m, 2H) 3.07-3.49 (m, 2H) 2.24-2.29 (m, 1 H) 1.61 (m, 1 H) 1.49 (m, 9H) 0.56-0.70(m, 4H) |
- 3
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[ 799557-87-2 ]
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[ 1262397-26-1 ]
-
[ 1445595-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
65% |
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100 - 150℃; Microwave irradiation; |
12
General procedure: To the solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspi ro[2 .4]heptane-5-carboxylate (prepared according to W0201 1006960, immol) in NMP (2m1/mmol), K2003(2mmol) and Ari-X (where X is ortho chloro orfluoro; 1.lmmol) were added. The reaction mixture was heated (microwave) at 100-150°C until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt;organics were collected, washed with water, dried and evaporated. Crude was purified bysilica gel chromatography (petroleum ether/ethyl acetate from 10/ito 3/1). |
65% |
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100 - 150℃; Microwave irradiation; |
3
General procedure: To the solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5-carboxylate (prepared according to WO2011006960, 1 mmol) in NMP (2 ml/mmol), K2CO3 (2 mmol) and Ar1-X (where X is ortho chloro or fluoro; 1.1 mmol) were added. The reaction mixture was heated (microwave) at 100-150° C. until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt; organics were collected, washed with water, dried and evaporated. Crude was purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 3/1). |
- 4
-
[ 89719-92-6 ]
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[ 1262397-26-1 ]
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[ 1445595-93-6 ]
Yield | Reaction Conditions | Operation in experiment |
36% |
With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 100℃;Microwave irradiation; |
General procedure: To the solution of (5)-tert-butyl 6-(aminomethyl)-5-azaspi ro[2 .4]heptane-5-carboxylate(prepared according toW020ii006960, immol) in DMF (2m1/mmol), K2C03(2mmol) andAri-X (where X is ortho chloro or fluoro; i.immol) were added. The reaction mixture was heated (microwave) at 80-100C until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt; organics were collected, washed with water, dried and evaporated. |
- 5
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[ 1262397-26-1 ]
-
[ 69045-82-5 ]
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[ 1431663-93-2 ]
Yield | Reaction Conditions | Operation in experiment |
86% |
With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 100℃;Microwave irradiation; |
General procedure: To the solution of (5)-tert-butyl 6-(aminomethyl)-5-azaspi ro[2 .4]heptane-5-carboxylate(prepared according toW020ii006960, immol) in DMF (2m1/mmol), K2C03(2mmol) andAri-X (where X is ortho chloro or fluoro; i.immol) were added. The reaction mixture was heated (microwave) at 80-100C until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt; organics were collected, washed with water, dried and evaporated. |
86% |
With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 100℃;Microwave irradiation; |
General procedure: To the solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5-carboxylate (prepared according to WO2011006960, 1 mmol) in DMF (2 ml/mmol), K2CO3 (2 mmol) and Ar1-X (where X is ortho chloro or fluoro; 1.1 mmol) were added. The reaction mixture was heated (microwave) at 80-100 C. until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt; organics were collected, washed with water, dried and evaporated. |
- 6
-
[ 1262397-26-1 ]
-
[ 72537-17-8 ]
-
[ 1445595-86-7 ]
Yield | Reaction Conditions | Operation in experiment |
60% |
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100 - 150℃;Microwave irradiation; |
General procedure: To the solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspi ro[2 .4]heptane-5-carboxylate (prepared according to W0201 1006960, immol) in NMP (2m1/mmol), K2003(2mmol) and Ari-X (where X is ortho chloro orfluoro; 1.lmmol) were added. The reaction mixture was heated (microwave) at 100-150C until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt;organics were collected, washed with water, dried and evaporated. Crude was purified bysilica gel chromatography (petroleum ether/ethyl acetate from 10/ito 3/1). |
60% |
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100 - 150℃;Microwave irradiation; |
General procedure: To the solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5-carboxylate (prepared according to WO2011006960, 1 mmol) in NMP (2 ml/mmol), K2CO3 (2 mmol) and Ar1-X (where X is ortho chloro or fluoro; 1.1 mmol) were added. The reaction mixture was heated (microwave) at 100-150 C. until complete conversion of the starting material. The resulting mixture was poured in aqueous solution of NaHCO3 and extracted with AcOEt; organics were collected, washed with water, dried and evaporated. Crude was purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 3/1). |