(3-Azido-2-methylpropenyl)-benzene → HCID 178438934, compound

HRID 384184Notes

Reaction equation

HRID 384184 reaction equation
[ClH:1].[CH2:2]([C:10]1[N:11]=[C:12]([NH2:15])[NH:13][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[CH:9].[N:16]([CH2:19][C:20]([CH3:28])=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N+:17]=[N-:18]>>[ClH:1].[CH3:28][C:20](=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:19][N:16]1[CH:9]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:10]2[N:11]=[C:12]([NH2:15])[NH:13][CH:14]=2)[N:18]=[N:17]1

Participants

3

Reactant 2

HCID 76639733(3-Azido-2-methylpropenyl)-benzeneHCID 178442669HCID 178442669, compound

Product 1

HCID 178438934HCID 178438934, compoundYield 85%

Procedure

4-Oct-7-ynyl-1H-imidazol-2-ylamine hydrochloride (0.098 g, 0.568 mmol) was reacted with (3-Azido-2-methyl-propenyl)-benzene (0.118 g, 0.681 mmol) following the general procedure for click reactions outlined above to produce 4-{6-[1-(2-Methyl-3-phenyl-allyl)-1H-[1,2,3]triazol-4-yl]-hexyl}-1H-imidazol-2-ylamine hydrochloride (0.147 g, 85%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.42 (s, 1H), δ 7.25-7.15 (m, 5H), δ 6.65 (s, 1H), δ 6.36 (s, 1H), δ 5.23 (s, 2H), δ 2.78 (t, 2H), δ 2.38 (t, 2H), δ 1.74 (s, 3H), δ 1.64 (m, 2H), δ 1.51 (m, 2H), δ 1.33 (m, 4H) ppm; 13C (75 MHz, CD3OD) δ 147.5, 136.3, 132.9, 132.8, 129.9, 128.9, 128.6, 128.5, 128.3, 127.7; HRMS (ESI) calcd for C21H29N6(M+) 365.2448, found 365.2448.

Sources & evidence

ORD record
ord-8a426d1c4a96453e84932a0478b58915
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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