Ethylamine → HCID 118159580, compound

HRID 628383Notes

Reaction equation

HRID 628383 reaction equation
[N:1]1([CH2:5][C:6]2[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=2)[CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:19]([CH3:22])=[N:20][N:21]=4)[C:13]=3[CH:12]=[C:11]2[C:23](O)=[O:24])[CH2:4][CH2:3][CH2:2]1.[CH:29]([N:32](CC)C(C)C)(C)[CH3:30].C(N)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:65]([OH:71])([C:67]([F:70])([F:69])[F:68])=[O:66]>CN1CCCC1=O.CC#N>[F:68][C:67]([F:70])([F:69])[C:65]([OH:71])=[O:66].[F:68][C:67]([F:70])([F:69])[C:65]([OH:71])=[O:66].[N:1]1([CH2:5][C:6]2[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=2)[CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:19]([CH3:22])=[N:20][N:21]=4)[C:13]=3[CH:12]=[C:11]2[C:23]([NH:32][CH2:29][CH3:30])=[O:24])[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118159634HCID 118159634, compound

Product 1

HCID 118159580HCID 118159580, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 6-[3-(azetidin-1-ylmethyl)benzyl]-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid (0.017 g, 0.045 mmol, from Step 7) in N-methylpyrrolidinone (1 mL) was added N,N-diisopropylethylamine (0.032 mL, 0.18 mmol) and ethylamine (0.010 g, 0.018 mmol, Aldrich), followed by the addition of HATU (0.022 g, 0.059 mmol). When the reaction was complete as determined by LCMS, the reaction was diluted with MeCN, and TFA was added to aid in solubility. The product was purified via preparative HPLC-MS (Waters SunFire C18, 5 μm 30×100 mm, (H2O, 0.1% TFA) MeOH, flow rate: 60 mL/min). Yield: (10 mg, 35%).

Workup

  1. additionwas added to aid in solubility
  2. customThe product was purified via preparative HPLC-MS (Waters SunFire C18, 5 μm 30×100 mm, (H2O, 0.1% TFA) MeOH, flow rate: 60 mL/min)

Sources & evidence

ORD record
ord-80508675e8384e2aa98b320f9961b5cd
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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