(3-Azido-2-methylpropenyl)-benzene → HCID 178438932, compound

HRID 384182Notes

Reaction equation

HRID 384182 reaction equation
Cl.[CH2:2]([C:8]1[N:9]=[C:10]([NH2:13])[NH:11][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]#[CH:7].[N:14]([CH2:17][C:18]([CH3:26])=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[N+:15]=[N-:16]>>[CH3:26][C:18](=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:17][N:14]1[CH:7]=[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:8]2[N:9]=[C:10]([NH2:13])[NH:11][CH:12]=2)[N:16]=[N:15]1

Participants

3

Reactant 2

HCID 76639733(3-Azido-2-methylpropenyl)-benzeneHCID 178442468HCID 178442468, compound

Product 1

HCID 178438932HCID 178438932, compoundYield 88%

Procedure

4-Hex-5-ynyl-1H-imidazol-2-ylamine hydrochloride (0.089 g, 0.4.47 mmol) was reacted with (3-Azido-2-methyl-propenyl)-benzene (0.085 g, 0.491 mmol) following the general procedure for click reactions outlined above to produce 4-{4-[1-(2-Methyl-3-phenyl-allyl)-1H-[1,2,3]triazol-4-yl]-butyl}-1H-imidazol-2-ylamine (0.132 g, 79%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.36 (s, 1H), 7.03 (m, 5H), 6.49 (s, 1H), 6.25 (s, 1H), 5.05 (s, 2H), 2.67 (t, 2H), δ 2.73 (t, 2H), δ 1.56 (s, 3H), δ 1.42 (m, 4H) ppm; 13C (75 MHz, CD3OD) δ 147.3, 144.7, 136.4, 132.7, 129.9, 128.9, 128.6, 128.5, 128.3, 127.5, 127.2, 126.9, 108.7, 61.2, 27.4, 27.3, 23.8, 22.8, 14.8 bpm; HRMS (ESI) calcd for C19H24N6(M+) 336.2135, found 336.2134.

Sources & evidence

ORD record
ord-b63cba046fea4413b81fc5e6fb6cc659
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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