1,1'-Carbonyldiimidazole → tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1397892Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>C1COCC1>[O:28]=[C:27]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=3)=[CH:3][C:2]=2[NH:1]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound 18 (0.58 g, 2 mmol) and CDI (0.34 g, 2.1 mmol) in THF (10 mL) was stirred at 60° C. for 6 h. The solvent was removed in vacuo, the residue was triturated with diethyl ether, and the resultant off-white solid was filtered and washed with diethyl ether to obtain compound 13. Yield: 68%, off-white solid, mp 244-245° C. IR (KBr, cm1) 3433, 3191 (CONH), 3037 (Ar—H), 2978 (Alph-H), 1713, 1689 (C=0), 1604, 1433 (C═C), 1244 (C—N), 1178 (C-0); 1H NMR (500 MHz, DMSO d6)g 1.39 (s, 9H, OC(CH3)3), 2.48 (br. s, 2H, CH2), 3.54 (m, 2H, CH2), 3.93 (br. s, 2H, CH2), 5.97 (br. s, 1H, CH), 6.86 (d, J=8.2 Hz, 1H, H-7), 6.95 (d, J=2.4 Hz, 1H, H-4), 6.99 (dd, J=2.4, 8.2 Hz, 1H, H-6), 10.60 (br. s, 2FI, NH). 13C NMR (125.7 MHz, DMSO d6) δ 26.84 (CH2), 28.28 (OC(CH3)3), 32.33 (CH), 42.80 (CH2), 79.08 (OC(CH3)3), 105.16 (CH), 108.52 (C-4), 117.67 (C-7), 129.20 (C-6), 130.04 (C-8), 133.28 (C-5/C-9), 134.81 (C-5/C-9), 154.73 (CO), 155.67 (CO). Anal. Calcd for C17H21N3O3: C, 64.74; H, 6.71; N, 13.32%. Found: C, 64.68; H, 6.76; N, 13.24%.

Workup

customThe solvent was removed in vacuo
customthe residue was triturated with diethyl ether
filtrationthe resultant off-white solid was filtered
washwashed with diethyl ether

Sources & evidence

ORD record: ord-6ffc90055ae347d2ae00954beebddc0e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901304B1

Reaction notes

Loading…