Propylamine → US9777003, Example 83
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.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)O[N:51]1[C:55]2N=CC=[CH:59][C:54]=2N=N1.C(N)CC>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]([NH:51][CH2:55][CH2:54][CH3:59])=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
7
Reactant 4
HCID 7852Propylamine
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 salt (0.013 g, 0.031 mmol, from Step 5) in DMF (0.5 mL) was added N,N-diisopropylethylamine (0.023 mL, 0.13 mmol) followed by N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.022 g, 0.059 mmol). After stirring for 2 minutes, 1-propanamine (0.011 mL, 0.13 mmol, Aldrich) was added. The reaction was stirred for 15 minutes, then was diluted with MeOH and purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (3.5 mg, 32%).
Workup
- stirringThe reaction was stirred for 15 minutes
- custompurified via preparative HPLC-MS (C18
- washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)
Sources & evidence
- ORD record
- ord-f1de9bf5b3e746c9865b85fa31994945
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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