Trifluoroacetic acid → HCID 118159926, compound

HRID 628389Notes

Reaction equation

HRID 628389 reaction equation
[N:1]1([CH2:5][C:6]2[CH:7]=[C:8]([CH:26]=[C:27]([Cl:29])[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:30]([N:33](CC)C(C)C)(C)C.Cl.CN.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:66]([OH:72])([C:68]([F:71])([F:70])[F:69])=[O:67]>CN1C(=O)CCC1.CC#N>[F:69][C:68]([F:71])([F:70])[C:66]([OH:72])=[O:67].[F:69][C:68]([F:71])([F:70])[C:66]([OH:72])=[O:67].[N:1]1([CH2:5][C:6]2[CH:7]=[C:8]([CH:26]=[C:27]([Cl:29])[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:33][CH3:30])=[O:24])[CH2:2][CH2:3][CH2:4]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118159763HCID 118159763, compound

Product 1

HCID 118159926HCID 118159926, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 6-[3-(azetidin-1-ylmethyl)-5-chlorobenzyl]-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid (0.035 g, 0.085 mmol, from Step 9) in NMP (2 mL) was added N,N-diisopropylethylamine (0.059 mL, 0.34 mmol), methylamine hydrochloride (9.9 mg, 0.15 mmol, Alfa Aesar) and HATU (0.042 g, 0.11 mmol). After 30 minutes, the reaction was complete, and the reaction mixture was diluted with MeCN and a small amount of TFA. The product was purified by preparative HPLC-MS (Waters SunFire C18, Sum 30×100 mm, H2O (0.1% TFA) MeOH @ 60 mL/min). Yield: (0.01 g, 30%).

Workup

  1. customThe product was purified by preparative HPLC-MS (Waters SunFire C18, Sum 30×100 mm, H2O (0.1% TFA) MeOH @ 60 mL/min)

Sources & evidence

ORD record
ord-57a68de5750a4aed86f3e9f01bee2fe9
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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