1,1'-Carbonyldiimidazole → HCID 66751995, compound

HRID 1785409Notes

Reaction equation

HRID 1785409 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH:16]=[C:15]([C:17]([OH:19])=O)[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])=[O:5])[CH3:2].[CH:26]1[N:30]=[CH:29][N:28]([C:31](N2C=NC=C2)=O)[CH:27]=1>C(#N)C>[CH3:29][N:28]([CH3:31])[CH2:27][CH2:26][NH:30][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:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:16]=1)=[O:19]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66752117HCID 66752117, compound

Product 1

HCID 66751995HCID 66751995, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

From acid 18i 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 (79%), mp 214-215° C. (from acetonitrile). 1H NMR (CDCl3): δ 1.28 (t, J=7.2 Hz, 3H, CO2CH2CH3), 2.29 [s, 6H, N(CH3)2], 2.62 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.87 (s, 3H, ArCH3), 3.72 (q, J=5.9 Hz, CH2CH2NMe2), 4.25 (q, J=7.1 Hz, CO2CH2CH3), 4.78 (s, 2H, CH2CO2Et), 7.51 (t, J=7.6 Hz, 1H, H-8), 7.74 (d, J=6.9 Hz, 1H, H-7), 7.87 (d, J=8.2 Hz, 1H, H-9), 8.53 (s, 1H, H-3), 9.28 (s, 1H, H-10), 10.96 (br t, J=4.8 Hz, 1H, CONH). 13C NMR (CDCl3): δ 13.7 (CO2CH2CH3), 18.1 (ArCH3), 37.3 (CH2CH2NMe2), 45.1 [N(CH3)2], 50.1 (CH2CO2Et), 58.4 (CH2CH2NMe2), 61.6 (CO2CH2CH3), 109.8 (C-4), 118.7 (C-10a), 125.5 (C-9a), 126.4 (CH, C-8), 126.9 (CH, C-9), 132.6 (CH, C-7), 135.6 (C-6), 139.6 (CH, C-10), 142.7 (CH, C-3), 147.8 (C-5a), 148.4 (C-4a), 162.0 (C-1), 163.9 (CONH), 166.9 (CO2Et).

Sources & evidence

ORD record
ord-d491207662d941299d86e4fb23131f2a
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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