Ethanolamine → Trifluoroacetic acid

HRID 1408483Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([OH:23])=O)=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.CN(C([O:42]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:59][CH2:60][CH2:61][OH:62].CN([CH:66]=[O:67])C>>[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([NH:59][CH2:60][CH2:61][OH:62])=[O:23])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[C:66]([OH:67])([C:2]([F:25])([F:24])[F:1])=[O:42]

Participants

Reactant 5

HCID 700Ethanolamine

HCID 6228Dimethylformamide

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 68627117HCID 68627117, compound

Product 2

HCID 6422Trifluoroacetic acidYield 82%

HCID 68628029HCID 68628029, compound

Procedure

4-(4-(trifluoromethoxy)phenylamino)quinazoline-7-carboxylic acid (30 mg, 0.09 mmol) was mixed with DIEA (30 uL, 0.172 mmol) and HATU (39 mg, 0.1 mmol) in 2 ml DMF at room temperature. 2-Aminoethanol (6.1 mg, 0.1 mmol) was added into the reaction mixture 0.5 hour later. After stirring at room temperature for 2 hours, the reaction mixture was concentrated and purified by prep-HPLC to afford the title compound as TFA salt (29 mg, 82% Yield). MS m/z 393.04 (M+1).

Workup

concentrationthe reaction mixture was concentrated
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-723773946c684c989ded82cee0048a43
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921336B2

Reaction notes

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