1,1'-Carbonyldiimidazole → HCID 118317160, compound

HRID 1497344Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH2:21][NH2:22].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1>[O:29]=[C:28]1[NH:22][CH2:21][C:3]2[C:2](=[CH:7][CH:6]=[C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:10][CH2:9]3)[CH:4]=2)[NH:1]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 17 (1.38 g, 4.5 mmol) in THF (20 mL) at room temperature was CDI (0.80 g, 4.95 mmol) and the reaction was stirred at 80° C. for 6 hr. The mixture was cooled to room temperature and the solid formed was filtered, washed with diethyl ether to afford 0.99 g (72%) of compound 10 as an off-white foam. IR (KBr) νmax. cm−1: 3210, 3162 (NH), 3032 (Ar—H), 1691 (C═O), 1607, 1515, 1419 (C═C). 1H NMR (500 MHz, CDCl3) δ=1.47 (s, 9H, (CH3)3C); 3.06 (m, 4H, 2CH2); 3.52 (m, 4H, 2CH2); 4.49 (s, 2H, CH2); 6.69 (m, 2H, aromatic-H), 6.74 (m, 1H, aromatic-H); 7.82 (br.s, 1H, NH); 13C NMR (125.7 MHz, CDCl3) δ=28.60 (CH3)3C), 43.35 (CH2), 43.90 (CH2), 50.66 (CH2), 80.10 (CH3)3C), 112.11 (aromatic-C), 112.28 (aromatic-C), 117.19 (aromatic-C), 130.18 (aromatic-C), 134.88 (aromatic-C), 143.18 (aromatic-C), 154.62 (CO), 155.93 (C═O). Calculated (%) for C17H24N4O3 (332.18); C, 61.43; H, 7.28; N, 16.86. found (%) C, 61.38; H, 7.32; N, 16.81.

Workup

customat room temperature
temperatureThe mixture was cooled to room temperature
customthe solid formed
filtrationwas filtered
washwashed with diethyl ether

Sources & evidence

ORD record: ord-45a61d0dbc28492dbad5a368f6d067ea
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199969B1

Reaction notes

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