1,1'-Carbonyldiimidazole → HCID 66752391, compound

HRID 1785414Notes

Reaction equation

HRID 1785414 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:21]=1)=[N:8][C:9]1[C:10]([C:18]([OH:20])=O)=[CH:11][N:12]([CH3:17])[C:13](=[O:16])[C:14]=1[CH:15]=2.[CH:22]1[N:26]=[CH:25][N:24]([C:27](N2C=NC=C2)=O)[CH:23]=1>C(#N)C>[CH3:25][N:24]([CH3:27])[CH2:23][CH2:22][NH:26][C:18]([C:10]1[C:9]2[N:8]=[C:7]3[CH:21]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]3=[CH:15][C:14]=2[C:13](=[O:16])[N:12]([CH3:17])[CH:11]=1)=[O:20]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66752687HCID 66752687, compound

Product 1

HCID 66752391HCID 66752391, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

From acid 18w, with a reflux time of 96 h and a recharge with an equal amount of CDI after 48 h, and obtained as a yellow solid (80%), mp 213-215° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.50 [s, 6H, N(CH3)2], 2.78 (t, J=6.0 Hz, 2H, CH2CH2NMe2), 3.67 (s, 3H, NCH3), 3.77 (q, J=5.8 Hz, 2H, CH2CH2NMe2), 4.02 (s, 3H, ArOCH3), 7.22 (dd, J=9.1, 2.2 Hz, 1H, H-8), 7.43 (d, J=2.2 Hz, 1H, H-6), 7.85 (d, J=9.1 Hz, 1H, H-9), 8.53 (s, 1H, H-3), 9.14 (s, 1H, H-10), 11.36 (br s, 1H, CONH). 13C NMR (CDCl3): δ 36.8 (CH2CH2NMe2 and NCH3), 45.0 [N(CH3)2], 55.6 (ArOCH3), 57.7 (CH2CH2NMe2), 105.3 (CH, C-6), 108.8 (C-4), 117.3 (C-10a), 120.9 (CH, C-8), 121.4 (C-9a), 130.0 (CH, C-9), 138.3 (CH, C-10), 143.1 (CH, C-3), 149.7 (C-4a), 150.9 (C-5a), 162.5 (C-1), 163.4 (C-7), 164.4 (CONH).

Sources & evidence

ORD record
ord-b84d4300df014e45a6e06a983e66eb4a
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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