1,1'-Carbonyldiimidazole → HCID 66752718, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:6][N:7]1[CH:16]=[C:15]([C:17](O)=[O:18])[C:14]2[N:13]=[C:12]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:11]3=[CH:10][C:9]=2[C:8]1=[O:25].[CH:31]1[N:35]=[CH:34][N:33]([C:36](N2C=NC=C2)=O)[CH:32]=1>C(#N)C>[CH3:34][N:33]([CH3:36])[CH2:32][CH2:31][NH:35][C:17]([C:15]1[C:14]2[N:13]=[C:12]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:11]3=[CH:10][C:9]=2[C:8](=[O:25])[N:7]([CH2:6][C:5]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:16]=1)=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
From acid 18r with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a yellow solid (85%), mp 213-214° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.22 [s, 6H, N(CH3)21, 2.52 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.63 (s, 3H, ArCH3), 3.62 (q, J=6.1 Hz, 2H, CH2CH2NMe2), 3.75 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 5.09 (s, 2H, CH2Ph), 6.74 (d, J=8.5 Hz, 1H, H-5′), 6.90-6.92 (m, 2H, H-2′, H-6′), 7.27 (t, J=7.6 Hz, 1H, H-8), 7.49 (d, J=6.8 Hz, 1H, H-7), 7.61 (d, J=8.1 Hz, 1H, H-9), 8.55 (s, 1H, H-3), 8.99 (s, 1H, H-10), 10.70 (br t, J=5.3 Hz, 1H, CONH). 13C NMR (CDCl3) δ 18.2 (ArCH3), 37.4 (CH2CH2NMe2), 45.2 (N(CH3)2], 51.9 (CH2Ph), 55.6 (OCH3), 55.7 (OCH3), 58.6 (CH2CH2NMe2), 109.6 (C-4), 111.1 (CH, C-5′), 111.5 (CH, C-6′), 119.1 (C-10a), 120.9 (CH, C-2′), 125.4 (C-9a), 126.2 (CH, C-8), 126.9 (CH, C-9), 128.2 (C-1′), 132.4 (CH, C-7), 135.5 (C-6), 139.5 (CH, C-10), 142.3 (CH, C-3), 147.6 (C-5a), 148.2 (C-4a), 148.9 (C-4′), 149.1 (C-3′), 162.1 (C-1), 164.1 (CONH).
Sources & evidence
- ORD record
- ord-ecc8105a4410432586f68ea2c5c93a5c
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504507B2
Reaction notes
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