Cyanamide → HCID 178441359, compound
Reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:10])[CH2:6][CH2:7][C:8]#[CH:9].[N:12]#[C:13][NH2:14]>>[ClH:1].[CH2:6]([C:5]1[N:10]=[C:13]([NH2:14])[NH:12][CH:4]=1)[CH2:7][C:8]#[CH:9]Participants
3
Procedure
2-Amino-hex-5-ynoic acid methyl ester hydrochloride (2.53 g, 14.2 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-But-3-ynyl-1H-imidazol-2-ylamine hydrochloride (1.17 g, 48%) as a pale yellow oil (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (300 MHz, CD3OD) δ 6.52 (s, 1H), δ 2.61 (t, 2H), δ 2.42 (m, 2H), δ 2.27 (t, 1H) ppm; 13C NMR (75 MHz, CD3OD) δ 147.4, 126.2, 109.4, 81.9, 69.9, 23.8, 17.4 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869, found 136.0865.
Sources & evidence
- ORD record
- ord-c941a8e43fb242cf8541f0892595cb26
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367713B2
Reaction notes
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