Cyanamide → HCID 178442468, compound

HRID 2283527Notes

Reaction equation

HRID 2283527 reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:12])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[N:14]#[C:15][NH2:16]>>[ClH:1].[CH2:6]([C:5]1[N:12]=[C:15]([NH2:16])[NH:14][CH:4]=1)[CH2:7][CH2:8][CH2:9][C:10]#[CH:11]

Participants

3

Reactant 2

HCID 9864CyanamideHCID 866350832-Amino-oct-7-ynoic acid methyl ester hydrochloride

Product 1

HCID 178442468HCID 178442468, compoundYield 87%

Procedure

2-Amino-oct-7-ynoic acid methyl ester hydrochloride (2.90 g, 14.1 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-Hex-5-ynyl-1H-imidazol-2-ylamine hydrochloride (2.45 g, 87%) as a pale yellow solid (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (300 MHz, CD3OD) δ 6.43 (s, 1H), δ 2.44 (t, 2H), 2.14 (t, 1H), δ 2.12 (m, 2H), δ 1.64 (m, 2H), δ 1.47 (m, 2H) ppm; 13C NMR (75 MHz, CD3OD) δ 147.3, 127.6, 108.5, 83.4, 68.7, 27.7, 27.1, 23.8, 17.5 ppm; HRMS (ESI) calcd for C9H14N3 (M+) 164.1182. Found 164.1182.

Sources & evidence

ORD record
ord-5d54ecd4a5384c738bc50cef9a58d546
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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