2-Amino-4-hept-6-ynyl-imidazole-1-carboxylic acid tert-butyl ester → HCID 91371723, compound

HRID 529959Notes

Reaction equation

HRID 529959 reaction equation
[NH2:1][C:2]1[N:3]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13])[N:6]=1.[N:21]([CH2:24][CH2:25][NH:26][C:27](=[O:40])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:30][CH:29]=1)=[N+:22]=[N-:23]>>[NH2:1][C:2]1[N:3]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[N:23]=[N:22][N:21]([CH2:24][CH2:25][NH:26][C:27](=[O:40])[C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:30][CH:29]=3)[CH:13]=2)[N:6]=1

Participants

3

Reactant 2

HCID 533595342-Amino-4-hept-6-ynyl-imidazole-1-carboxylic acid tert-butyl esterHCID 57914405HCID 57914405, compound

Product 1

HCID 91371723HCID 91371723, compound

Procedure

tert-butyl 2-amino-4-(hept-6-ynyl)-1H-imidazole-1-carboxylate (0.097 g, 0,349 mmol) was reacted with N-(2-azidoethyl)-4-hexylbenzamide (0.096 g, 0.349 mmol) following the general click procedure to give tert-butyl 2-amino-4-(5-(1-(2-(4-hexylbenzamido)ethyl)-1H-1,2,3-triazol-4-yl)pentyl)-1H-imidazole-1-carboxylate 1H NMR (300 MHz, CDCl3) δ 7.65 (d, J=8.1 Hz, 2H), δ 7.55 (t, J=6.7 Hz, 1H), δ 7.26 (s, 1H), δ 7.09 (d, J=7.8 Hz, 2H), δ 6.39 (s, 1H), δ 6.04 (s, 2H), δ 4.48 (t, J=4.8 Hz, 2H), δ 3.83 (q, J=5.6, 4.8 Hz, 2H), δ 2.56 (q, J=7.5, 8.1 Hz, 4H), δ 2.24 (t, J=6.9 Hz, 2H), δ 1.50 (m, 13H), δ 1.21 (m, 1H), δ 0.77 (t, J=5.7 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 168.3, 148.3, 147.3, 138.7, 131.4, 128.7, 127.4, 122.2, 106.4, 84.9, 73.9, 49.5, 40.2, 36.0, 31.8, 31.3, 29.9, 29.3, 29.1, 28.9, 28.2, 28.1, 28.0, 25.6, 22.8, 14.3 ppm; HRMS (ESI) calcd for C30H45N7O3 (M+) 551.3584. found 551.3581, which was subsequently deprotected to give N-(2-(4-(5-(2-amino-1H-imidazol-4-yl)pentyl)-1H-1,2,3-triazol-1-yl)ethyl)-4-hexylbenzamide hydrochloride (0.164 g, 96% yield). 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), δ 7.67 (d, J=7.6 Hz, 2H), δ 7.21 (d, J=7.6 Hz, 2H), δ 6.43 (s, 1H), δ 4.72 (s, 2H), δ 3.87 (s, 2H), δ 2.74 (s, 2H), δ 2.58 (t, J=7.6 Hz, 2H), δ 2.31 (t, J=6.8 Hz, 2H), δ 1.66 (s, 2H), δ 1.55 (s, 4H), δ 1.35 (s, 2H), δ 1.25 (s, 6H), δ 0.66 (t, J=8.8 Hz, 3H) ppm; 13C NMR (100 MHz, CD3OD) δ 169.2, 159.5, 147.4, 147.3, 131.2, 108.4, 51.2, 48.5, 48.3, 48.1, 47.9, 47.7, 47.5, 47.3, 39.5, 36.5, 35.6, 31.6, 31.7, 31.2, 28.8, 28.2, 27.9, 27.7, 24.1, 23.9, 22.6, 13.3, 9.9 ppm; HRMS (ESI) calcd for C25H37N7O (M+) 451.3059. found 451.3058.

Sources & evidence

ORD record
ord-c0d24974f59040beb9b558cda30685fb
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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