Triethylamine → N-(2-Methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl)-3-(pyrimidin-2-yl)pyridine-2-carboxamide
Reaction equation
[CH3:1][C:2]1([NH:22][C:23]2[N:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25]N=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8]([C:10]1[C:15]([C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9].[CH3:33]C1(NC2C=CC(C(F)(F)F)=CN=2)CCCC1N.N1C=CC=NC=1C1C(C(O)=O)=NC=CC=1.C(N(CC)CC)C>>[CH3:1][C:2]1([NH:22][C:23]2[CH:33]=[CH:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][N:28]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8]([C:10]1[C:15]([C:16]2[N:17]=[CH:18][CH:19]=[CH:20][N:21]=2)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9]Participants
Reactant 4
Product 1
Procedure
Prepared according to the procedure for N-(2-methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)-3-(pyrimidin-2-yl)pyridine-2-carboxamide (Example 153) from 1-methyl-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine (Intermediate 51; 91 mg, 0.35 mmol), 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 85 mg, 0.42 mmol) and triethylamine (0.147 ml, 1.06 mmol) except after work-up the organics were loaded directly on to a cation/anion mixed mode cartridge, eluted with DCM then with 2M ammonia in methanol and concentrated in vacuo. The resulting residue was purified by reverse phase chromatography (C18 silica, 5-100% water (0.05% ammonia)/acetonitrile) then recrystallised from MTBE/heptane to afford the title compound.
Workup
- customPrepared
- additionmixed mode cartridge
- washeluted with DCM
- concentrationwith 2M ammonia in methanol and concentrated in vacuo
- customThe resulting residue was purified by reverse phase chromatography (C18 silica, 5-100% water (0.05% ammonia)/acetonitrile)
- customthen recrystallised from MTBE/heptane
Sources & evidence
- ORD record
- ord-c0e05aa72a35478bb8d5afa70443cc6d
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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