Trifluoroacetic acid → HCID 178521197, compound
Reaction equation
[Cl:1][C:2]1[N:7]([CH2:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:20]=[CH:21][N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:23]=2)=[O:10])[C:6](=[O:43])[C:5]([NH:44][CH2:45][C:46]([F:54])([F:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)=[N:4][CH:3]=1.C([SiH](CC)CC)C.[F:62][C:63]([F:68])([F:67])[C:64]([OH:66])=[O:65]>>[OH:66][C:64]([C:63]([F:68])([F:67])[F:62])=[O:65].[Cl:1][C:2]1[N:7]([CH2:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)=[O:10])[C:6](=[O:43])[C:5]([NH:44][CH2:45][C:46]([F:53])([F:54])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)=[N:4][CH:3]=1Participants
Procedure
To a solution of 2-[6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-N-[2-(1-trityl-1H-imidazol-4-yl)-benzyl]-acetamide (47 mg, 0.058 mmol) in trifluoroacetic acid (1.5 ml) was added triethylsilane (excess) until completion of the reaction. Concentration and purification by reverse phase preparative HPLC (5% to 95% CH3CN in water containing 0.1% TFA, C18 PRO YMC 20×150 mm) gave 2-[6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-N-[2-(1H-imidazol-4-yl)-benzyl]-acetamide TFA salt; 1H NMR (CD3OD, 400 MHz) δ 8.95 (d, 1H, J=1.3 Hz), 8.63 (d, 1H, J=4.1 Hz), 7.94 (dt, 1H, J=7.7 Hz, J=1.6 Hz), 7.70 (m, 2H), 7.51 (m, 6H), 6.83 (s, 1H), 4.80 (s, 2H), 4.46 (s, 2H), 4.28 (t, 2H, J=14.1 Hz); MS (ES+) M+1 500.4 for C23H20ClF2N7O2.
Workup
- customuntil completion of the reaction
- concentrationConcentration and purification by reverse phase preparative HPLC (5% to 95% CH3CN in water containing 0.1% TFA
Sources & evidence
- ORD record
- ord-775b9606417e427f991834189c82d6a9
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026324B2
Reaction notes
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