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CAS No. : | 1143532-39-1 | MDL No. : | MFCD22628785 |
Formula : | C21H25ClN6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JDUBGYFRJFOXQC-KRWDZBQOSA-N |
M.W : | 428.92 | Pubchem ID : | 25227436 |
Synonyms : |
AZD5363
|
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.5% | With N-ethyl-N,N-diisopropylamine In butan-1-ol at 60℃; for 18 h; | Example 9 alternative route 1: (S)-4-amino-N-Q-(4-chlorophenyl)-3-hvdroxypropyl)- l-(7H-pyrrolo [2,3-dl pyrimidin-4-yl)piperidine-4-carboxamideN-Ethyldiisopropylamine (1.676 ml, 9.62 mmol) was added to (S)-4-amino-N-(l-(4- chlorophenyl)-3-hydroxypropyl)piperidine-4-carboxamide (Intermediate 49) (Ig, 3.21 mmol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.493 g, 3.21 mmol) in butan-1-ol (15 ml). The resulting solution was stirred at 600C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (25 mL) and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 6percent MeOH with ammonia in DCM. Pure fractions were evaporated to dryness to afford (S)-4-amino-N-(l-(4-chlorophenyl)-3-hydroxypropyl)-l-(7H-pyrrolo[2,3- d]pyrimidin-4-yl)piperidine-4-carboxamide (842mg) as a white foam. (S)-4-amino-N-(l- (4-chlorophenyl)-3-hydroxypropyl)-l-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4- carboxamide was stirred in ethyl acetate (7 mL) for 18 hours. The solid was collected by filtration, washed with a small amount of ethyl acetate and vacuum oven dried at 55°C for 18 hours to afford (S)-4-amino-N-(l-(4-chlorophenyl)-3-hydroxypropyl)-l-(7H- pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (0.585 g, 42.5 percent) as a white solid, m/z (ES+) (M+H)+ = 429; HPLC tR= 1.60 min. IH NMR (400.13 MHz, DMSO-d6) δ 1.39 - 1.47 (2H, m), 1.80 - 2.02 (4H, m), 2.17 (2H, s), 3.35 - 3.40 (2H, m), 3.50 - 3.59 (2H, m), 4.34 - 4.41 (2H, m), 4.53 (IH, t), 4.88 (IH, d), 6.57 (IH, m), 7.14 - 7.16 (IH, m), 7.31 - 7.37 (4H, m), 8.12 (IH, s), 8.42 (IH, d), 11.62 (IH, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.4% | With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 16 h; | Example 9: (S)-4-amino-N-Q-(4-chlorophenyl)-3-hvdroxypropyl)-l-(7H-pyrrolo[2.,3- dl pyrimidin-4-yl)piperidine-4-carboxamide (E9)HCl (4M in Dioxane) (3.00 mL, 12.00 mmol) was added to (S)-tert-butyl 4-(l-(4- chlorophenyl)-3-hydroxypropylcarbamoyl)- 1 -(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin- 4-ylcarbamate (Intermediate 22) (1.27 g, 2.40 mmol) in dichloromethane (20 mL). The resulting suspension was stirred at 20 0C for 16 hours. The reaction mixture was filtered through a PTFE filtercup and the crude solid was purified by preparative HPLC (Waters XTerra Cl 8 column, 5μm silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent TFA) and MeCN as eluents. Fractions containing the desired compound were purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3ZMeOH and pure fractions were evaporated to dryness to afford (S)-4-amino-N-(l-(4-chlorophenyl)-3- hydroxypropyl)-l-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (0.200 g, 19.4 percent) as a white solid. IH NMR (399.9 MHz, DMSO-d6) δ 1.45 (2H, d), 1.86 (IH, d), 1.90 - 1.93 (IH, m), 2.19 (2H, s), 3.38 (2H, q), 3.51 - 3.58 (2H, m), 4.35 - 4.38 (2H, m), 4.53 (IH, t), 4.88 (IH, d), 6.58 (IH, t), 7.16 (IH, t), 7.32 - 7.38 (4H, m), 8.12 (IH, s), 8.43 (IH, d), 11.63 (IH, s), m/z (ESI+) (M+H)+ = 429; HPLC tR = 1.46 min. |