1,1'-Carbonyldiimidazole → HCID 66752428, compound

HRID 1785413Notes

Reaction equation

HRID 1785413 reaction equation
[CH3:1][C:2]1[C:7]2=[N:8][C:9]3[C:10]([C:24]([OH:26])=O)=[CH:11][N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[C:13](=[O:16])[C:14]=3[CH:15]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:27]1[N:31]=[CH:30][N:29]([C:32](N2C=NC=C2)=O)[CH:28]=1>C(#N)C>[CH3:30][N:29]([CH3:32])[CH2:28][CH2:27][NH:31][C:24]([C:10]1[C:9]2[N:8]=[C:7]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]3=[CH:15][C:14]=2[C:13](=[O:16])[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:11]=1)=[O:26]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66752792HCID 66752792, compound

Product 1

HCID 66752428HCID 66752428, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

From acid 18t, with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a bright yellow solid (75%), mp 183-184° C., (from acetonitrile). 1H NMR (CDCl3): δ 2.25 [s, 6H, N(CH3)2], 2.57 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.67 (s, 3H, ArCH3), 3.66 (q, J=6.1 Hz, CH2, CH2CH2NMe2), 5.30 (s, 2H, CH2Pyr), 7.10 (dd, J=7.0, 5.2 Hz, 1H, H-5′), 7.26-7.33 (m, 2H, H-3′, H-8), 7.52-7.59 (m, 2H, H-4′, H-7), 7.64 (d, J=8.2 Hz, 1H, H-9), 8.46 (d, J=4.4 Hz, 1H, H-6′), 8.66 (s, 1H, H-3), 9.02 (s, 1H, H-10), 10.79 (br t, J=5.1 Hz, 1H, CONH). 13C NMR (CDCl3): δ 18.3 (ArCH3), 37.3 (CH2CH2NMe2), 45.2 [N(CH3)2], 53.7 (CH2Pyr), 58.6 (CH2CH2NMe2), 109.6 (C-4), 119.1 (C-10a), 122.1 (CH, C-3′), 122.7 (CH, C-5′), 125.5 (C-9a), 126.4 (CH, C-8), 127.0 (CH, C-9), 132.6 (CH, C-7), 135.6 (C-6), 136.7 (CH, C-4′), 139.6 (CH, C-10), 143.4 (CH, C-3), 147.7 (C-5a), 148.5 (C-4a), 149.6 (CH, C-6′), 155.0 (C-2′), 162.2 (C-1), 164.3 (CONH).

Sources & evidence

ORD record
ord-3434aa35b32a4373aabfc97172b9b4ca
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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