3-(Azidomethyl)thiophene → HCID 178479120, compound

HRID 384160Notes

Reaction equation

HRID 384160 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[CH:19]=[CH:18][S:17][CH:16]=1)=[N+:12]=[N-:13]>>[ClH:1].[S:17]1[CH:18]=[CH:19][C:15]([CH2:14][N:11]2[CH:4]=[C:3]([CH2:2][C:5]3[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=3)[N:13]=[N:12]2)=[CH:16]1

Participants

3

Reactant 2

HCID 147088083-(Azidomethyl)thiopheneHCID 178439632HCID 178439632, compound

Product 1

HCID 178479120HCID 178479120, compoundYield 44%

Procedure

4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (0.096 (0.061 mmol) was reacted with 3-azidomethyl thiophene (0.102 g, 0.732 mmol) following the general procedure for click reactions outlined above to produce 4-(1-Thiophen-3-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-1Himidazol-2-ylamine hydrochloride (0.079 g, 44%) of a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.18 (s, 1H), δ 7.44 (s, 1H), δ 7.30 (d, 1H), δ 6.98 (d, 1H), δ 6.53 (s, 1H), δ 5.57 (s, 2H), δ 3.95 (s, 2H) ppm; 13C (75 MHz, CD3OD) δ 145.7, 145.1, 143.7, 139.7, 129.8, 121.8, 111.5, 109.8, 109.2, 52.7, 21.5 ppm; HRMS (ESI) calcd for C11H12N6S (M+) 260.0919, found 260.0919.

Sources & evidence

ORD record
ord-c8ce7d792f8841c0a448ecfc61f1f1fe
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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