Triethylamine → 1-(5-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-(3-(4-fluorophenoxy)phenyl)-4-methylpiperidine-4-carboxamide
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:13][C:14]([C:16]3([CH3:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:26]1[C:27]2[C:34]([Cl:35])=[CH:33][NH:32][C:28]=2[N:29]=[CH:30][N:31]=1.C(N(CC)CC)C>C(O)(C)C>[Cl:35][C:34]1[C:27]2[C:26]([N:19]3[CH2:18][CH2:17][C:16]([CH3:22])([C:14]([NH:13][C:9]4[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]5[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=5)[CH:8]=4)=[O:15])[CH2:21][CH2:20]3)=[N:31][CH:30]=[N:29][C:28]=2[NH:32][CH:33]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
N-(3-(4-Fluorophenoxy)phenyl)-4-methylpiperidine-4-carboxamide from step B (50 mg, 0.13 mmol), 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine from step C (19 mg, 0.1 mmol), and triethylamine (0.04 mL, 0.3 mmol) were combined in isopropanol (1 mL) and heated at 130° C. for 30 minutes under microwave conditions. The product was isolated by prep HPLC to give the title compound.
Workup
- customThe product was isolated by prep HPLC
Sources & evidence
- ORD record
- ord-bc079b1fb60a4c609e7c6b03dc4e4d03
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193202B2
Reaction notes
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