2-Amino-4-hept-6-ynyl-imidazole-1-carboxylic acid tert-butyl ester → HCID 123465823, compound

HRID 529964Notes

Reaction equation

HRID 529964 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:42])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[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:42])[C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[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 86659555HCID 86659555, compound

Product 1

HCID 123465823HCID 123465823, compound

Procedure

tert-butyl 2-amino-4-(hept-6-ynyl)-1H-imidazole-1-carboxylate (0.078 g, 0.282 mmol) was reacted with N-(2-azidoethyl)-4-octylbenzamide (0.085 g, 0.282 mmol) following the general click procedure to give tert-butyl 2-amino-4-(5-(1-(2-(4-octylbenzamido)ethyl)-1H-1,2,3-triazol-4-yl)pentyl)-1H-imidazole-1-carboxylate 1H NMR (300 MHz, CDCl3) δ 7.64 (s, 2H), δ 7.47 (s, 1H), δ 7.21 (s, 1H), δ 7.09 (s, 2H), δ 6.47 (bs, 3H), δ 4.48 (s, 2H), δ 3.84 (s, 2H), δ 2.53 (s, 4H), δ 2.28 (t, J=15.9 Hz, 2H), δ 1.51 (bs, 6H), δ 1.18 (bs, 10H), 0.77 (t, J=6.6 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 180.7, 180.2, 168.3, 147.4, 142.4, 139.2, 131.4, 128.8, 127.4, 107.4, 49.6, 40.2, 36.1, 32.1, 31.4, 29.9, 29.6, 29.5, 28.8, 28.2, 28.1, 25.4, 22.9, 14.3 ppm; HRMS (ESI) calcd for C32H49N7O3 (M+) 579.3896. found 579.3890, 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-octylbenzamide hydrochloride (0.097 g, 67% yield). 1H NMR (400 MHz, CD3OD) δ 7.65 (s, 2H), δ 7.23 (s, 3H), δ 6.45 (s, 1H), δ 3.97 (s, 4H), δ 2.60 (s, 4H), δ 2.47 (s, 2H), δ 1.57 (m, 6H), δ 1.27 (bm, 12H), δ 0.83 (t, J=6.4 Hz, 3H) ppm; 13C NMR (100 MHz, CD3OD) δ 183.5, 172.0, 169.3, 161.8, 153.9, 147.4, 131.2, 128.5, 127.7, 127.3, 119.1, 108.8, 104.7, 94.6, 63.4, 38.7, 35.6, 31.8, 31.3, 29.3, 29.2, 29.1, 28.1, 27.7, 27.1, 24.2, 22.5, 13.3, 12.6 ppm; HRMS (ESI) calcd for C27H41N7O (M+) 479.3372. found 479.3378.

Sources & evidence

ORD record
ord-80ca39b6dbbc4979ac06ba30ef69d1d8
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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