Pyridine → HCID 22479779, compound

HRID 1353795Notes

Reaction equation

HRID 1353795 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:16]=2)=[N:2]1.N1C=CC=CC=1.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44].[OH-].[NH4+]>>[NH:2]1[C:3]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[O:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:43](=[O:45])[CH3:44])[CH2:26][CH2:25]2)=[N:4][CH:5]=[N:1]1

Participants

6

Reactant 5

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 178420715HCID 178420715, compound

Product 1

HCID 22479779HCID 22479779, compoundYield 9%

Procedure

1-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))-3-(2-piperazinylethoxy)benzene (0.066 g, 0.169 mmol) was stirred with pyridine (0.50 mL, 6.18 mmol), triethylamine (0.10 mL, 0.717 mmol) and acetic anhydride (0.10 mL, 1.06 mmol) at ambient temperature. After 2 h, ammonium hydroxide (0.50 mL) was added and the mixture stirred for 1 h. The mixture was evaporated and gave the title compound (0.0064 g, 9% yield). 1H NMR (CD3OD) δ 8.71 (s, 1H), 8.35 (s, 1H), 8.08 (dd, 1H), 7.66 (d, 1H), 7.61 (dt, 1H), 7.55 (m, 1H), 7.44 (t, 1H), 7.01 (m, 1H), 4.25 (t, 2H), 3.58 (dt, 4H), 2.85 (t, 2H), 2.60 (dt, 4H), 2.08 (s, 3H). ES-MS (m/z) 432 [M+1]+

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-843a94ca74f744e99bac70394ee4ef99
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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