Trifluoroacetic acid → HCID 68314130, compound

HRID 2069119Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:42])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31](=[O:41])[CH2:32][NH:33]C(=O)OC(C)(C)C)[CH:25]=3)=[CH:15][CH:14]=2)[N:7]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][CH2:32][C:31]([NH:30][C:26]1[CH:25]=[C:24]([O:23][C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]([NH:12][C:11]([NH:10][C:8]3[N:7]([C:43]4[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=3)=[O:42])=[CH:14][CH:15]=2)[CH:29]=[CH:28][N:27]=1)=[O:41]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of tert-butyl 2-(4-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-ylamino)-2-oxoethylcarbamate (187 mg, 92% pure, 0.259 mmol) in dry DCM (6 mL) 0° C. under nitrogen was added TFA (2.0 mL) and the reaction mixture maintained at 0° C. for 20 min and then warmed to RT for 3 hr. The resulting mixture was evaporated in vacuo and the residue was purified by SCX capture and release to afford the title compound, Intermediate G1, as a brown solid (130 mg, 87%); Rt 1.82 min (Method 2); m/z 564 (M+H)+ (ES+).

Workup

temperaturewarmed to RT for 3 hr
customThe resulting mixture was evaporated in vacuo
customthe residue was purified by SCX capture and release

Sources & evidence

ORD record: ord-6cbe11acfd924ca8bca859c8e7042c0b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299074B2

Reaction notes

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