Cyanamide → HCID 178442669, compound

HRID 598628Notes

Reaction equation

HRID 598628 reaction equation
[ClH:1].CO[C:4](=O)[CH:5]([NH2:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13].[N:16]#[C:17][NH2:18]>>[ClH:1].[CH2:6]([C:5]1[N:14]=[C:17]([NH2:18])[NH:16][CH:4]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13]

Participants

3

Reactant 2

HCID 9864CyanamideHCID 866350872-Amino-dec-9-ynoic acid methyl ester hydrochloride

Product 1

HCID 178442669HCID 178442669, compoundYield 53%

Procedure

2-Amino-dec-9-ynoic acid methyl ester hydrochloride (1.50 g, 6.42 mmol) was treated to an Akabori reduction followed by a cyanamide condensation employing conditions previously reported to produce 4-Oct-7-ynyl-1H-imidazol-2-ylamine hydrochloride (0.774 g, 53%) as a pale yellow solid (Olofson et al., Journal of Organic Chemistry 1997, 62, (23), 7918-7919). 1H NMR (400 MHz, CD3OD) δ 6.09 (s, 1H), δ 2.19 (t, 2H), δ 1.95 (t, 1H), 1.93 (m, 2H), δ 1.39-1.11 (m, 8H) ppm; 13C NMR (75 MHz, CD3OD) δ 148.5, 131.0, 110.1, 83.9, 68.3, 28.6, 28.5, 28.4, 28.3, 25.7, 17.8 ppm; HRMS (ESI) calcd for C11H18N3 (M+) 192.1495. found 192.1495.

Sources & evidence

ORD record
ord-e9567d334a9240ffbb7c011b303bde55
Source dataset
uspto-grants-2011_03
Patent number
US07897631B2

Reaction notes

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