HCID 178480163, compound → HCID 178511883, compound
Reaction equation
CN1CCCC1CCN1CCCCC2C=C(NC(C3SC=CC=3)=N)C=CC1=2.O=[C:29]1[N:35]([CH2:36][CH2:37][N:38]2[CH2:43]C[CH2:41][CH2:40][CH2:39]2)[C:34]2[CH:44]=[CH:45][C:46]([NH:48][C:49]([C:51]3[S:52][CH:53]=[CH:54][CH:55]=3)=[NH:50])=[CH:47][C:33]=2CC[CH2:30]1>>[N:38]1([CH2:37][CH2:36][N:35]2[C:34]3[C:33](=[CH:47][C:46]([NH:48][C:49]([C:51]4[S:52][CH:53]=[CH:54][CH:55]=4)=[NH:50])=[CH:45][CH:44]=3)[CH2:30][CH2:29]2)[CH2:39][CH2:40][CH2:41][CH2:43]1Participants
Procedure
A solution of compound 3 (0.40 g, 1.531 mmol) and Pd—C (0.162 g, 0.153 mmol, 10% wt) in dry ethanol (5 mL) was purged with hydrogen gas. The reaction was stirred at room temperature over night under hydrogen atm. (balloon pressure). Then the reaction mixture was filtered through a celite pad and washed with ethanol (35 mL). The filtrate (compound 4) was treated with imidate 5 (0.873 g, 3.06 mmol) and stirred over night at room temperature. The reaction was diluted with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel: 2% methanol: 98% CH2Cl2 followed by 5% 2M NH3 in methanol: 95% CH2Cl2, to give a greenish/yellow solid (230 mg, 44%). 1H-NMR (DMSO-d6) δ 7.68 (dd, J=0.9, 3.6 Hz, 1H), 7.55 (dd, J=0.9, 5.1 Hz, 1H), 7.07 (dd, J=3.6, 4.8 Hz, 1H), 6.62 (s, 1H), 6.50-6.45 (m, 2H), 6.23 (s, 2H), 3.33-3.27 (m, 2H), 3.11 (t, J=6.9 Hz, 2H), 2.84 (t, J=8.1 Hz, 2H), 2.62 (t, J=7.5, 2H), 2.55-2.45 (m, 4H), 1.70-1.65 (m, 4H); ESI-MS (m/z, %): 341 (MH+, 100), 244 (45), 127 (57), 98 (38); ESI-HRMS calculated for C19H25N4S (MH+): Calculated: 341.1794, Observed: 341.1788; HPLC purity: 95.3%.
Sources & evidence
- ORD record
- ord-08216cd32607451794c3461b058cf47f
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173813B2
Reaction notes
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