HCID 57914348, compound → HCID 178479125, compound

HRID 529901Notes

Reaction equation

HRID 529901 reaction equation
[ClH:1].[CH2:2]([C:6]1[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=1)[CH2:3][C:4]#[CH:5].[N:12]([CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)=[N+:13]=[N-:14]>>[ClH:1].[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][N:12]2[CH:5]=[C:4]([CH2:3][CH2:2][C:6]3[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=3)[N:14]=[N:13]2)=[CH:17]1

Participants

3

Reactant 2

HCID 57914348HCID 57914348, compoundHCID 178441359HCID 178441359, compound

Product 1

HCID 178479125HCID 178479125, compoundYield 58.3%

Procedure

4-But-3-ynyl-1H-imidazol-2-ylamine hydrochloride (0.073 g, 0.429 mmol) was reacted with 3-azidomethyl-indole (0.089 g, 0.515 mmol) following the general procedure for click reactions outlined above to produce 4-{2-[1-(1H-Indol-3-ylmethyl)-1H-[1,2,3]triazol-4-yl}-ethyl]-1Himidazol-2-ylamine hydrochloride (0.086 g, 58%) as a yellow oil. 1H NMR (300 MHz, CD3OD) δ 8.11 (s, 1H), δ 7.84 (m, 2H), δ 7.41 (m, 2H), δ 7.06 (d, 1H), δ 5.66 (s, 2H), δ 3.04 (t, 2H), δ 2.85 (t, 2H) ppm; 13C (75 MHz, CD3OD) δ 147.5, 144.9, 144.8, 134.7, 131.9, 127.2, 127.1, 127.1, 125.8, 125.3, 124.4, 109.5, 49.9, 23.6, 23.2 ppm; HRMS (ESI) calcd for C17H19N7 (M+) 321.1701. found 321.1704.

Sources & evidence

ORD record
ord-3a2c706a1367426ab154804dee555734
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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