Pyrrolidine → N-(((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methylpiperidin-1-yl)(pyrrolidin-1-yl)-methylene)cyanamide
Reaction equation
C1C=CC(OC(OC2C=CC=CC=2)=[N:9][C:10]#[N:11])=CC=1.C[CH2:20][N:21]([CH:25]([CH3:27])C)[CH:22]([CH3:24])C.Cl.[CH3:29][C@@H:30]1[CH2:35][CH2:34][NH:33][CH2:32][C@@H:31]1[C:36]1[N:40]2[C:41]3[CH:47]=[CH:46][NH:45][C:42]=3[N:43]=[CH:44][C:39]2=[CH:38][N:37]=1.N1CCCC1>CC#N>[C:36]1([C@@H:31]2[C@H:30]([CH3:29])[CH2:35][CH2:34][N:33]([C:20]([N:21]3[CH2:22][CH2:24][CH2:27][CH2:25]3)=[N:11][C:10]#[N:9])[CH2:32]2)[N:40]2[C:41]3[CH:47]=[CH:46][NH:45][C:42]=3[N:43]=[CH:44][C:39]2=[CH:38][N:37]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of diphenyl cyanocarbonimidate (0.163 g, 0.685 mmol) and DIEA (0.239 mL, 1.371 mmol) in MeCN (5 mL) was added 1-((3R,4R)-4-methylpiperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (0.20 g, 0.68 mmol). The reaction was heated at about 80° C. for about 2 h. The reaction mixture was concd in vacuo. The residue was dissolved in pyrrolidine (1.0 mL, 12 mmol) and transferred to a sealed microwave vessel. The reaction was heated at about 120° C. for about 30 min in a CEM microwave. The reaction mixture was concd in vacuo and purified by RP-HPLC (Table 1, Method i) to give N-(((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methylpiperidin-1-yl)(pyrrolidin-1-yl)-methylene)cyanamide (0.030 g, 11%): LC/MS (Table 1, Method b) Rt=1.62 min; m/z: 377 (M+H)+
Workup
- customtransferred to a sealed microwave vessel
- temperatureThe reaction was heated at about 120° C. for about 30 min in a CEM microwave
- custompurified by RP-HPLC (Table 1, Method i)
Sources & evidence
- ORD record
- ord-e727d4015015478e854d35f2914dbf5d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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