Trifluoroacetic acid → HCID 25216419, compound

HRID 2196538Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:44]=[CH:43][CH:42]=[CH:41][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C:14]2[CH:15]=[C:16]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28](C)[C:29](=O)OC(C)(C)C)[CH2:22][CH2:21]3)[CH:17]=[CH:18][CH:19]=2)[N:12]=[C:11]([C:37]([F:40])([F:39])[F:38])[CH:10]=1)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:44]=[CH:43][CH:42]=[CH:41][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][NH:28][CH3:29])[CH2:22][CH2:21]3)[CH:15]=2)[N:12]=[C:11]([C:37]([F:38])([F:39])[F:40])[CH:10]=1)=[O:8]

Participants

Conditions

Temperature: 21 °C

Procedure

To a stirred solution of 70 (20 mg, 0.032 mmol) in CH2Cl2 (650 μl) was added TFA (50 μl, 0.650 mmol). The resulting solution was allowed to stir at 21° C. for 1.5 h. After the usual work-up, the residue was purified by preparative TLC using 10% MeOH/CH2Cl2. The title product 71 (16 mg, 79% yield) was isolated as a white solid. 1H NMR (CD3OD) δ(ppm): 7.38-7.36 (m, 3H), 7.27-7.24 (m, 2H), 7.14 (s, 1H), 7.12 (s, 1H), 6.94 (d, 1H, J=8.0 Hz), 6.87 (t, 1H, J=7.2 HZ), 4.44 (s, 2H), 3.81 (s, 3H), 3.13 (t, 2H, J=5.6 Hz), 3.05 (d, 2H, J=11.6 Hz), 2.72 (s, 3H), 2.67 (t, 2H, J=6.0 Hz), 2.61-2.59 (m, 1H), 2.22 (td, 2H, J=2.8, 12.0 Hz), 1.83-1.77 (m, 4H). LRMS (ESI): calc. 515.6; found 516.8 (MH)+.

Workup

customAfter the usual work-up, the residue was purified by preparative TLC

Sources & evidence

ORD record: ord-bcfd9443fdb440a49241a69cbb06e368
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338437B2

Reaction notes

Loading…