Triethylamine → HCID 58964267, compound

HRID 1626201Notes

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.[NH2:45][C:46]1[CH:60]=[CH:59][C:49]([O:50][CH2:51][CH2:52][N:53]2[CH2:57][CH2:56][C@H:55]([OH:58])[CH2:54]2)=[C:48]([C:61]2[N:62]([CH3:66])[N:63]=[CH:64][CH:65]=2)[CH:47]=1>C1COCC1>[OH:58][C@H:55]1[CH2:56][CH2:57][N:53]([CH2:52][CH2:51][O:50][C:49]2[CH:59]=[CH:60][C:46]([NH:45][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:47][C:48]=2[C:61]2[N:62]([CH3:66])[N:63]=[CH:64][CH:65]=2)[CH2:54]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of HATU (183 mg, 0.482 mmol), triethylamine (100 μl, 0.741 mmol) and 4-trifluoromethyl benzoic acid (92 mg, 0.482 mmol) in THF (1.0 mL) was stirred at room temperature. After 15 min, (S)-1-{2-[4-Amino-2-(2-methyl-2H-pyrazol-3-yl)-phenoxy]-ethyl}-pyrrolidin-3-ol (112 mg, 0.370 mmol) was added, and the mixture was stirred at 100° C. for 10 minutes in microwave. The mixture was purified by HPLC to give the title compound as a white solid (TFA salt, 58 mg, 33% yield). 1H NMR (DMSO-d6, 400 MHz) δ 1.67-1.74 (m, 1H), 1.78-1.90 (m, 1H), 2.09-2.18 (m, 1H), 2.88-2.97 (m, 1H), 3.31-3.37 (m, 1H), 3.47-3.61 (m, 2H), 3.69 (s, 3H), 4.31-4.36 (m, 4H), 6.31 (s, 1H), 7.24-7.28 (m, 1H), 7.50 (s, 1H), 7.75 (s, 1H), 7.90 (d, J=8.84 Hz, 1H), 7.94 (d, J=8.34 Hz, 2H), 8.16 (d, J=8.34 Hz, 2H), 9.93-10.11 (m, 1H), 10.5 (s, 1H). Exact mass calculated for C24H25F3N4O3 474.2, found 475.3 (MH+).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-2478a8fcfc0947878a3564e5079049bb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785441B2

Reaction notes

Loading…