Cyanamide → HCID 178439632, compound

HRID 384151Notes

Reaction equation

HRID 384151 reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:9])[CH2:6][C:7]#[CH:8].[N:11]#[C:12][NH2:13]>>[ClH:1].[CH2:6]([C:5]1[N:9]=[C:12]([NH2:13])[NH:11][CH:4]=1)[C:7]#[CH:8]

Participants

3

Reactant 2

HCID 9864CyanamideHCID 53399010Methyl 2-aminopent-4-ynoate hydrochloride

Product 1

HCID 178439632HCID 178439632, compoundYield 59%

Procedure

2-Amino-pent-4-ynoic acid methyl ester hydrochloride (2.91 g, 17.8 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (1.65 g, 59%) as a yellow oil (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (300 MHz, CD3OD) δ 6.30 (s, 1H), δ 5.02 (d, 2H), δ 2.26 (t, 1H) ppm; 13C NMR (75 MHz, CD3OD) δ 150.1, 127.2, 109.6, 83.6, 69.8, 15.9 ppm; HRMS (ESI) calcd for C6H7N3 (M+) 122.0712, found 122.0713.

Sources & evidence

ORD record
ord-7a819443d8684add8a7892f8eb0b4148
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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