Trifluoroacetic acid → HCID 49857170, compound

HRID 1510835Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][N:28]=[C:27]4[NH:33][C:34]([C@@H:36]3[CH2:40][CH2:39][CH2:38][N:37]3C(OC(C)(C)C)=O)=[O:35])=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][N:28]=[C:27]4[NH:33][C:34]([C@@H:36]3[CH2:40][CH2:39][CH2:38][NH:37]3)=[O:35])=[CH:20][CH:19]=2)=[CH:16][N:17]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86653896HCID 86653896, compound

Product 1

HCID 49857170HCID 49857170, compoundYield 73%

Procedure

(S)-tert-Butyl 2-(5-(4-(2-((S)-1-(tert-butoxycarbonyl)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)-1H-indazol-3-ylcarbamoyl)pyrrolidine-1-carboxylate was deprotected with TFA by the method given in Step 2 of Example 11. Obtained a light yellow solid (183 mg, ca. 73%). 1H NMR (500 MHz, CD3OD) δ 8.16 (s, 1H), 7.88 (app d, J=8.2 Hz, 2H), 7.84 (s, 1H), 7.76-7.79 (m, 3H), 7.59 (d, J=8.9 Hz, 1H), 5.10 (unresolved dd, J=7.9, 8.9 Hz, 1H), 4.63 (unresolved dd, J=7.3, 8.2 Hz, 1H), 3.51-3.62 (m, 3H), 3.43-3.48 (m, 1H), 2.62-2.69 (m, 2H), 2.48-2.55 (m, 1H), 2.15-2.40 (m, 1H). LCMS: Anal. Calcd. for C25H27N7O: 441; found: 442 (M+H)+.

Sources & evidence

ORD record: ord-9d2953ae5ee34459b633d4456977c0af
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211928B2

Reaction notes

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