Dimethylformamide → Trifluoroacetic acid

HRID 1362968Notes

Reaction equation

HRID 1362968 reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=O.[CH3:45][N:46]1[C:50]([C:51]2[CH:52]=[C:53]([NH2:65])[CH:54]=[CH:55][C:56]=2[O:57][CH2:58][CH2:59][N:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)=[CH:49][CH:48]=[N:47]1.CN([CH:69]=[O:70])C>>[CH3:45][N:46]1[C:50]([C:51]2[CH:52]=[C:53]([NH:65][C:37](=[O:39])[C:36]3[CH:40]=[CH:41][CH:42]=[C:34]([C:33]([F:32])([F:44])[F:43])[CH:35]=3)[CH:54]=[CH:55][C:56]=2[O:57][CH2:58][CH2:59][N:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)=[CH:49][CH:48]=[N:47]1.[C:69]([OH:70])([C:33]([F:44])([F:43])[F:32])=[O:8]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 99633-(Trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 468324843-(1-methyl-1H-pyrazol-5-yl)-4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine

Product 2

HCID 6422Trifluoroacetic acidHCID 11612277[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide

Conditions

Temperature
100 °C

Procedure

A solution of HATU (113 mg, 0.30 mmol), triethylamine (55.7 μl, 0.400 mmol) and 3-trifluoromethyl-benzoic acid (57 mg, 0.30 mmol) in DMF (1.0 mL) was stirred at room temperature. After 15 min, 3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (57.0 mg, 0.200 mmol) was added, and the mixture was stirred at 100° C. for 10 minutes in microwave. The mixture was purified by HPLC to give title compound as a burgundy on (TFA salt, 42 mg, 46% yield). Exact mass calculated for C24H25F3N4O2 458.2. found 459.4 (MH+).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-d415cfa773df4b7981fac7e17aef7bef
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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