Diisopropylethylamine → 4'-Methyl-N-(1-(2-methylthiazol-4-yl)ethyl)-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([OH:23])=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:25][C:26]1[S:27][CH:28]=[C:29]([CH:31]([NH2:33])[CH3:32])[N:30]=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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([NH:33][CH:31]([C:29]3[N:30]=[C:26]([CH3:25])[S:27][CH:28]=3)[CH3:32])=[O:23])[CH:9]=2)=[CH:6][CH:7]=1Participants
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 216676501-(2-Methylthiazol-4-yl)-ethylamine hydrochloride
HCID 581879754'-Methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
A 20 mL vial was charged with 4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (30 mg, 0.097 mmol), 1-(2-Methylthiazol-4-yl)-ethylamine hydrochloride (22 mg, 0.12 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (92 mg, 0.24 mmol), N,N-diisopropylethylamine (0.068 mL, 0.39 mmol), and N,N-dimethylformamide (1.0 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was purified by preparative HPLC to get the product as a light peach colored solid.
Workup
- customThe reaction mixture was purified by preparative HPLC
- customto get the product as a light peach
Sources & evidence
- ORD record
- ord-2e6b80e302484c2687da84d032298453
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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