Diisopropylethylamine → 4'-Methyl-N-((R)-1-(2-methylpyrimidin-5-yl)ethyl)-5-(octahydropyrrolo[1,2-a]pyrazine-2-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[CH2:21][CH2:20][N:19]4[CH2:22][CH2:23][CH2:24][CH:18]4[CH2:17]3)=[O:15])[CH:11]=[C:10]([C:25]([OH:27])=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:28][C:29]1[N:34]=[CH:33][C:32]([C@H:35]([NH2:37])[CH3:36])=[CH:31][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:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:21][CH2:20][N:19]4[CH2:22][CH2:23][CH2:24][CH:18]4[CH2:17]3)=[O:15])[CH:11]=[C:10]([C:25]([NH:37][C@@H:35]([C:32]3[CH:31]=[N:30][C:29]([CH3:28])=[N:34][CH:33]=3)[CH3:36])=[O:27])[CH:9]=2)=[CH:4][CH:3]=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 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamine
HCID 581881564'-Methyl-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)biphenyl-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4′-methyl-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)biphenyl-3-carboxylic acid (50 mg, 0.14 mmol) in N,N-dimethylformamide (1.0 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (35 mg, 0.25 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (120 μL, 0.69 mmol). The reaction mixture was stirred for 16 hours at 25° C. The reaction mixture was purified by preparative HPLC to afford the final product as a light yellow solid.
Workup
- customThe reaction mixture was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-955a48c0550543a5b750961730a45bf7
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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