Dimethylformamide → Trifluoroacetic acid

HRID 1408478Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([CH2:20][CH2:21][C:22]([OH:24])=O)[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:43]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:60]1([CH2:66][CH2:67][NH2:68])[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1.CN([CH:72]=[O:73])C>>[N:60]1([CH2:66][CH2:67][NH:68][C:22](=[O:24])[CH2:21][CH2:20][N:17]2[C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=4)[C:12]=3[CH:19]=[CH:18]2)[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1.[C:72]([OH:73])([C:2]([F:26])([F:25])[F:1])=[O:43]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 4082852-Morpholinoethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 49780997HCID 49780997, compound

Product 2

HCID 6422Trifluoroacetic acid

HCID 42633115HCID 42633115, compound

Procedure

3-[4-(4-Trifluoromethoxy-phenylamino)-pyrrolo[2,3-d]pyrimidin-7-yl]-propionic acid (25 mg, 0.068 mmol) was mixed with DIEA (0.030 ml, 0.172 mmol) and HATU (28.5 mg, 0.071 mmol) in 2 ml DMF at room temperature. 2-Morpholin-4-yl-ethylamine (9.7 uL, 0.074 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. MS m/z 479.2 (M+1).

Workup

concentrationthe reaction mixture was concentrated
custompurified by Prep-HPLC

Sources & evidence

ORD record: ord-58f8368be243407c87221e6d3b5d5058
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921336B2

Reaction notes

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