Trifluoroacetic acid → 1-{3-Chloro-4-[2-(2,4-difluoro-benzylamino)-ethoxy]-phenyl}-3-(5-cyano-pyrazin-2-yl)-urea

HRID 1019740Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[C:26]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[N:36][C:35]([C:38]#[N:39])=[CH:34][N:33]=2)=[O:30])[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23])C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>O1CCCC1>[Cl:1][C:2]1[CH:27]=[C:26]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[N:36][C:35]([C:38]#[N:39])=[CH:34][N:33]=2)=[O:30])[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][NH:7][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of tert-butyl 2-(2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)phenoxy)ethyl-(2,4-difluorobenzyl)carbamate (0.53 g, 0.95 mmol) in tetrahydrofuran (5 mL) at 0° C. was added trifluoroacetic acid (1.19 g, 9.5 mmol), and the resulting mixture was heated at 40° C. for 12 hours. The solvent was removed under reduced pressure to leave a residue that was purified by preparative HPLC (Preparative HPLC Method 1) to give the title compound (44 mg, 10%).

Workup

customThe solvent was removed under reduced pressure
customto leave a residue that
customwas purified by preparative HPLC (Preparative HPLC Method 1)

Sources & evidence

ORD record: ord-18a7e7958bc24cd3aed2a87869150310
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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