Trifluoroacetic acid → HCID 178462101, compound

HRID 1049149Notes

Reaction equation

HRID 1049149 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[C:8]([CH2:10][C:11]1([N:32]2[CH:36]=[C:35](B3OC(C)(C)C(C)(C)O3)[CH:34]=[N:33]2)[CH2:14][N:13]([C:15]2[C:29]([F:30])=[CH:28][C:18]([C:19]([NH:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[O:20])=[C:17]([F:31])[CH:16]=2)[CH2:12]1)#[N:9].Br[C:47]1[C:48]([CH2:52][OH:53])=[N:49][NH:50][CH:51]=1>>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[C:8]([CH2:10][C:11]1([N:32]2[CH:36]=[C:35]([C:47]3[C:48]([CH2:52][OH:53])=[N:49][NH:50][CH:51]=3)[CH:34]=[N:33]2)[CH2:12][N:13]([C:15]2[C:29]([F:30])=[CH:28][C:18]([C:19]([NH:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:24])[F:25])=[O:20])=[C:17]([F:31])[CH:16]=2)[CH2:14]1)#[N:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1317360004-{3-(Cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-2,5-difluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamideHCID 178520055HCID 178520055, compound

Product 1

HCID 178462101HCID 178462101, compound

Procedure

This compound was prepared as TFA salt by using procedures analogous to those described for the synthesis of Example 4, Step 6 starting from 4-{3-(cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-2,5-difluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamide and (4-bromo-1H-pyrazol-3-yl)methanol. LCMS calculated for C22H21F5N7O2 (M+1)+: m/z=510.2. Found: 510.0.

Sources & evidence

ORD record
ord-329fea9c0b63432caa0d150a0b8783d0
Source dataset
uspto-grants-2016_07
Patent number
US09382231B2

Reaction notes

Loading…