Dimethylamine → US9777003, Example 94
Reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:24]([CH3:27])=[N:25][N:26]=3)[C:18]=2[CH:17]=[C:16]1[C:28]([OH:30])=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:31]([N:34](CC)[CH:35](C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CNC.C1COCC1>CN(C=O)C.CO>[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:24]([CH3:27])=[N:25][N:26]=3)[C:18]=2[CH:17]=[C:16]1[C:28]([N:34]([CH3:35])[CH3:31])=[O:30])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
8
Reactant 5
HCID 674Dimethylamine
HCID 8028Tetrahydrofuran
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 1181594706-benzyl-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid trifluoroacetateProduct 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-benzyl-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid trifluoroacetate (0.015 g, 0.036 mmol, from Example 83, Step 5) in DMF (0.3 mL) was added N,N-diisopropylethylamine (0.058 mL, 0.33 mmol) followed by N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.048 g, 0.12 mmol). After stirring for 2 minutes, 2.0 M dimethylamine in THF (0.14 mL, 0.28 mmol, Aldrich) was added. After 15 minutes reaction time, the reaction was diluted with MeOH and purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (1.2 mg, 10%).
Workup
- customAfter 15 minutes reaction time
- custompurified via preparative HPLC-MS (C18
- washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)
Sources & evidence
- ORD record
- ord-4745e9639bd94fd7874615ef3692b89d
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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