Toluene → HCID 178437415, compound

HRID 1729439Notes

Reaction equation

[C:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:10]([CH2:12][CH3:13])=[N:11][C:6]2=[C:5]([CH3:32])[CH:4]=1)#[N:2].C[Sn]([N:37]=[N+:38]=[N-:39])(C)C.C1(C)C=CC=CC=1>CN(C=O)C>[CH2:12]([C:10]1[N:9]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:7]2=[N:8][C:3]([C:1]3[NH:39][N:38]=[N:37][N:2]=3)=[CH:4][C:5]([CH3:32])=[C:6]2[N:11]=1)[CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-Cyano-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (54 mg), trimethylstannyl azide (79 mg), toluene (5 mL), and DMF (1 mL) was heated to 110° C. for 24 hour. Concentration and purification (SiO2, 70/30/1CH2Cl2 /MeOH/NH4OH) gave 47 mg solid. 1H NMR (300 MHz, CD3OD) δ 7.93 (s, 1H), 7.56-7.38 (m, 4H), 7.14-7.05 (AB quartet, 4H), 5.61 (s, 2H), 2.86 (q, H, J=7.5 Hz), 2.71 (s, 3H), 1.27 (t, 3H, J=7.5 Hz)

Workup

concentrationConcentration and purification (SiO2, 70/30/1CH2Cl2 /MeOH/NH4OH)

Sources & evidence

ORD record: ord-da5d09e0af6b41c1a75dda187387c5a3
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332744

Reaction notes

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