2-(azidomethyl)-1H-benzo[d]imidazole → HCID 178478669, compound

HRID 384163Notes

Reaction equation

HRID 384163 reaction equation
[ClH:1].[CH2:2]([C:5]1[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=1)[C:3]#[CH:4].[N:11]([CH2:14][C:15]1[NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[N:16]=1)=[N+:12]=[N-:13]>>[ClH:1].[ClH:1].[NH:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[CH2:14][N:11]1[CH:4]=[C:3]([CH2:2][C:5]2[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=2)[N:13]=[N:12]1

Participants

3

Reactant 2

HCID 155637102-(azidomethyl)-1H-benzo[d]imidazoleHCID 178439632HCID 178439632, compound

Product 1

HCID 178478669HCID 178478669, compoundYield 59%

Procedure

4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (0.091 g, 0.576 mmol) was reacted with 2-azidomethyl-1H-benzimidazole, which was synthesized using previously reported methods (Hiales et al., Synthesis 1978, 4, 313-315), (0.120 g, 0.691 mmol) following the general procedure for click reactions outlined above to produce 4-[1-(1H-Benzoimidazol-2-ylmethyl)-1H-[1,2,3]triazol-4-ylmethyl]1Himidazol-2-ylamine dihydrochloride (0.125 g, 59%) of a yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.01 (s, 1H), δ 7.58 (d, 2H), δ 7.31 (t, 2H), δ 6.44 (s, 1H), δ 5.98 (s, 2H) δ 3.84 (s, 2H) ppm; 13C (75 MHz, CD3OD) δ 135.6, 124.7, 123.7, 123.5, 122.8, 112.8, 112.3, 108.4, 83.6, 78.9, 74.0, 73.2, 44.2, 19.3 ppm; HRMS (ESI) calcd for C14H14N8(M+) 295.1414, found 295.1420.

Workup

  1. customwas synthesized
  2. custommethods (Hiales et al., Synthesis 1978, 4, 313-315), (0.120 g, 0.691 mmol)

Sources & evidence

ORD record
ord-e139bf68a09148caa0a408a7e289ae0c
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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