Trifluoroacetic acid → US9611269, Example 26

HRID 571508Notes

Reaction equation

HRID 571508 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([CH2:10][C:11]1([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][N:35](COCC[Si](C)(C)C)[C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:14][N:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:12]1)#[N:9].Cl.[CH3:47][CH:48]([NH2:53])[C:49]([F:52])([F:51])[F:50]>>[C:8]([CH2:10][C:11]1([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][NH:35][C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:14][N:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:53][CH:48]([CH3:47])[C:49]([F:52])([F:51])[F:50])=[O:21])=[CH:17][CH:16]=2)[CH2:12]1)#[N:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18364314(RS)-2-Amino-1,1,1-trifluoropropane hydrochlorideHCID 711436124-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-azetidin-1-yl}benzoic acid

Product 1

HCID 71143548US9611269, Example 26

Procedure

This compound was prepared as TFA salt by using procedures analogous to those described for the synthesis of Example 19, Step 3 started from 4-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}benzoic acid and 1-methyl-2,2,2-trifluoroethylamine hydrochloride (SynQuest Labs: Cat. #93130-7-08). LCMS (M+H)+: m/z=495.2.

Workup

  1. customthose described for the synthesis of Example 19, Step 3

Sources & evidence

ORD record
ord-985a1ae25407424d9aba5ed88058ae79
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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