Cyanamide → 4-Pent-4-ynyl-1H-imidazol-2-ylamine hydrochloride
Reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:11])[CH2:6][CH2:7][CH2:8][C:9]#[CH:10].[N:13]#[C:14][NH2:15]>>[ClH:1].[CH2:6]([C:5]1[N:11]=[C:14]([NH2:15])[NH:13][CH:4]=1)[CH2:7][CH2:8][C:9]#[CH:10]Participants
3
Procedure
2-Amino-hept-6-ynoic acid methyl ester hydrochloride (2.00 g, 10.4 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-Pent-4-ynyl-1H-imidazol-2-ylamine hydrochloride (1.75 g, 90%) as a pale oil (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (300 MHz, CDCl3) δ 6.68 (bs, 2H), δ 6.24 (s, 1H), δ 2.51 (t, 2H), δ 2.17 (t, 1H), δ 1.95 (s, 1H), δ 1.74 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 148.3, 132.7, 111.6, 84.4, 69.1, 28.0, 26.0, 18.2 ppm; HRMS (ESI) calcd for C10H16N3(M+) 150.1026, found 150.1029.
Sources & evidence
- ORD record
- ord-6880682afadf4dff942fecd2076a5fd3
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367713B2
Reaction notes
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