Cyanamide → HCID 178442541, compound

HRID 2283528Notes

Reaction equation

HRID 2283528 reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12].[N:15]#[C:16][NH2:17]>>[ClH:1].[CH2:6]([C:5]1[N:13]=[C:16]([NH2:17])[NH:15][CH:4]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12]

Participants

3

Reactant 2

HCID 9864CyanamideHCID 866350852-Amino-non-8-ynoic acid methyl ester hydrochloride

Product 1

HCID 178442541HCID 178442541, compoundYield 53%

Procedure

2-Amino-non-8-ynoic acid methyl ester hydrochloride (2.02 g, 9.20 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-Hept-6-ynyl-1H-imidazol-2-ylamine hydrochloride (1.04 g, 53%) as a pale yellow solid (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (300 MHz, CD3OD) δ 6.17 (s, 1H), δ 2.19 (t, 2H), δ 1.90 (t, 1H), δ 1.86 (m, 2H), δ 1.24-1.13 (m, 6H) ppm; 13C NMR (75 MHz, CD3OD) δ 147.5, 128.3, 108.8, 83.8, 65.5, 28.4, 28.3, 28.2, 24.5, 17.8 ppm; HRMS (ESI) calcd for C10H16N3 (M+) 178.1338. Found 178.1337.

Sources & evidence

ORD record
ord-23990abb920e47a8a371b0ddadc65b91
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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