Trifluoroacetic acid → HCID 86635697, compound

HRID 598874Notes

Reaction equation

HRID 598874 reaction equation
CC([C:5]1[N:6]=[C:7]([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH:41]=[N:40][CH:39]=[CH:38]3)[S:8][C:9]=1[N:10]([CH2:14][C@@H:15]([NH:27]C(OC(C)(C)C)=O)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)C(=O)[O-])(C)C.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]>>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[NH2:27][C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:14][NH:10][C:9]1[S:8][C:7]([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH:41]=[N:40][CH:39]=[CH:38]3)=[N:6][CH:5]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86635698HCID 86635698, compound

Product 1

HCID 86635697HCID 86635697, compoundYield 64%

Procedure

To a 250 mL round-bottomed flask containing 1,1-dimethylethyl((2S)-2-((((1,1-dimethylethyl)oxy)carbonyl)-amino)-3-(4-(trifluoromethyl)phenyl)propyl)(2-(6-isoquinolinyl)-1,3-thiazol-5-yl)carbamate (8.9 mg, 0.014 mmol) was added TFA (1 mL). The mixture was stirred at room temperature 1 hour and evaporated. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 110 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 5% to 100% over 15 minutes, to provide the product (4.9 mg, 64% yield) as a brown oil. 1H NMR (400 MHz, CD3OD) δ ppm 3.11-3.20 (m, 2H), 3.43-3.51 (m, 2H), 3.77-3.84 (m, 1H), 7.12 (s, 1H), 7.55 (d, J=8.02 Hz, 2H), 7.71 (d, J=8.22 Hz, 2H), 8.37 (d, J=6.65 Hz, 1H), 8.43 (s, 3H), 8.49 (d, J=6.65 Hz, 1H), 9.59 (s, 1H). HRMS Theoretical (M+H) 429.13553, found 429.13603.

Workup

  1. customevaporated
  2. customThe crude product was purified by reverse-phase preparative HPLC
  3. customover 15 minutes

Sources & evidence

ORD record
ord-fe024b8f725248c5872bc4cf487a47a7
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…