Diisopropylethylamine → (R)-2'-Cyano-5-(4-cyanopyridin-3-yl)-4'-methyl-N-(1-morpholinopropan-2-yl)biphenyl-3-carboxamide
Reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[C:22]#[N:23])[CH:13]=[C:12]([C:24](O)=[O:25])[CH:11]=1)#[N:2].Cl.[O:28]1[CH2:33][CH2:32][N:31]([CH2:34][C@H:35]([NH2:37])[CH3:36])[CH2:30][CH2:29]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[C:22]#[N:23])[CH:13]=[C:12]([C:24]([NH:37][C@H:35]([CH3:36])[CH2:34][N:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[O:25])[CH:11]=1)#[N:2]Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 584493912'-Cyano-5-(4-cyanopyridin-3-yl)-4'-methylbiphenyl-3-carboxylic acid
HCID 67310127(R)-1-Morpholinopropan-2-amine hydrochlorideProduct 1
Reagents, catalysts & solvents 1
Procedure
A round bottom flask was charged with 2′-cyano-5-(4-cyanopyridin-3-yl)-4′-methylbiphenyl-3-carboxylic acid (20 mg, 0.059 mmol), (R)-1-morpholinopropan-2-amine hydrochloride (112 mg, 0.62 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (49 mg, 0.13 mmol), N,N-diisopropylethylamine (360 μL, 2.1 mmol), N,N-dimethylformamide (0.555 mL) and the reaction was stirred overnight at room temperature. The mixture was purified by HPLC to get the title compound as a light yellow solid.
Workup
- customThe mixture was purified by HPLC
Sources & evidence
- ORD record
- ord-88c99c96f5d042f9946f51679478457c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133122B2
Reaction notes
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