Ethanolamine → Trifluoroacetic acid

HRID 1408480Notes

Reaction equation

HRID 1408480 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[CH:19]=[C:18]([C:20]([OH:22])=O)[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.CN(C([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:58][CH2:59][CH2:60][OH:61].CN([CH:65]=[O:66])C>>[OH:61][CH2:60][CH2:59][NH:58][C:20]([C:18]1[S:17][C:13]2[N:14]=[CH:15][N:16]=[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:9][CH:8]=3)[C:12]=2[CH:19]=1)=[O:22].[C:65]([OH:66])([C:2]([F:24])([F:23])[F:1])=[O:41]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42634389HCID 42634389, compound

Product 2

HCID 6422Trifluoroacetic acidYield 61%HCID 42633119HCID 42633119, compound

Procedure

4-(4-(trifluoromethoxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid (30 mg, 0.08 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 (25 mg, 61% Yield). 1H NMR 400 MHz (DMSO-d6) δ 10.10 (s, 1H), 9.26 (s, 1H), 8.82 (s, 1H), 8.21 (d, 2H, J=8.8 Hz), 7.85 (d, 2H, J=8.8 Hz), 7.34 (s, 1H), 3.02 (t, 2H, J=6.4 Hz), 2.65 (t, 2H, J=6.4 Hz). MS m/z 399.12 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-878a4fd298eb4bf0b8cf49b9d3968d91
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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