Triethylamine → HCID 11503810, compound

HRID 1362967Notes

Reaction equation

CN(C(ON1N=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:42]=[CH:41][C:37]([C:38]([OH:40])=O)=[CH:36][CH:35]=1.[CH3:45][N:46]1[C:50]([C:51]2[CH:52]=[C:53]([NH2:66])[CH:54]=[CH:55][C:56]=2[O:57][CH2:58][CH2:59][N:60]2[CH2:65][CH2:64][O:63][CH2:62][CH2:61]2)=[CH:49][CH:48]=[N:47]1>C1COCC1>[CH3:45][N:46]1[C:50]([C:51]2[CH:52]=[C:53]([NH:66][C:38](=[O:40])[C:37]3[CH:36]=[CH:35][C:34]([C:33]([F:32])([F:44])[F:43])=[CH:42][CH:41]=3)[CH:54]=[CH:55][C:56]=2[O:57][CH2:58][CH2:59][N:60]2[CH2:65][CH2:64][O:63][CH2:62][CH2:61]2)=[CH:49][CH:48]=[N:47]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of HATU (98.0 mg, 0.260 mmol), triethylamine (55.7 μl, 0.400 mmol) and 4-trifluoromethyl-benzoic acid (49.0 mg, 0.260 mmol) in THF (1.0 mL) was stirred at room temperature. After 15 min, 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenylamine (60.0 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 white solid (TFA salt, 27 mg, 28%). 1H NMR (DMSO-d6, 400 MHz) δ 2.96-3.10 (m, 2H), 3.16-3.19 (m, 2H), 3.52-3.60 (m, 4H), 3.70 (s, 3H), 3.84-3.87 (m, 2H), 4.39 (t, J=5.05 Hz, 2H), 6.31 (d, J=1.77 Hz, 1H), 7.28 (d, J=9.09 Hz, 1H), 7.51 (d, J=1.77 Hz, 1H), 7.75 (d, J=2.78 Hz, 1H), 7.94 (d, J=8.34 Hz, 2H), 8.16 (d, J=8.84 Hz, 2H), 8.89 (s, 1H), 10.5 (s, 1H). Exact mass calculated for C24H25F3N4O3 474.2. found 475.4 (M+).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-da79a83002d543e3886a6289509d7ece
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884101B2

Reaction notes

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