Trifluoroacetic acid → HCID 86634411, compound

HRID 1690502Notes

Reaction equation

C(OC([NH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][N:28]=2)=[CH:22][CH:21]=1)[C:10]([NH:12][C:13]1[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:8][C@@H:9]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][N:28]=2)=[CH:22][CH:21]=1)[C:10]([NH:12][C:13]1[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=1)=[O:11]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86634412HCID 86634412, compound

Product 1

HCID 86634411HCID 86634411, compoundYield 34%

Procedure

Using an analogous procedure to that described in the second paragraph of Example 21, (2S)-2-(N-tert-butoxycarbonylamino)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]-N-(4,5-dimethylthiazol-2-yl)acetamide was reacted with trifluoroacetic acid to give the title compound in 34% yield; 1H NMR: (DMSOd6) 2.13 (s, 3H), 2.21 (s, 3H), 3.97 (s, 3H), 3.98 (s, 3H), 4.64 (s, 1H), 7.25 (d, 2H), 7.38 (s, 1H), 7.54 (m, 3H), 8.53 (s, 1H); Mass Spectrum: M+H+466.

Sources & evidence

ORD record: ord-d3d0558e3a11450bba923c144fb3727d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153643B2

Reaction notes

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