Hydrazine → N-{4-[4-(4-chlorobenzyl)-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]pyridin-2-yl}acetamide

HRID 2401716Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([C:16]([NH2:18])=O)=[C:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:12]=2[C:27]#[N:28])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].COC(OC)[N:32]([CH3:34])C.[NH2:37]N>C1(C)C=CC=CC=1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:13]2[C:12]([C:27]#[N:28])=[C:11]([C:9]3[CH:8]=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=3)[S:15][C:14]=2[C:16]2[NH:18][CH:34]=[N:32][N:37]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-[2-(acetylamino)pyridin-4-yl]-3-(4-chlorobenzyl)-4-cyanothiophene-2-carboxamide (0.030 g, 0.073 mmol) in toluene (0.75 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (0.0970 mL, 0.730 mmol), and the mixture was stirred at 100° C. for 90 minutes. The mixture was concentrated and the residue was dissolved in acetic acid (0.75 mL). Hydrazine (0.0114 mL, 0.365 mmol) was added and the mixture was stirred at 100° C. for 1 hour. The mixture was concentrated and the residue was treated with water. The precipitate was collected, washed with water and dried in a vacuum oven to yield the title compound (0.016 g, 48%). LCMS: (FA) ES+, 435. 1H NMR (400 MHz, d6-DMSO) δ: 10.76 (s, 1H), 8.77 (s, 1H), 8.54-8.46 (m, 2H), 7.50-7.47 (m, 1H), 7.37-7.26 (m, 4H), 4.63 (s, 2H), 2.12 (s, 3H).

Workup

concentrationThe mixture was concentrated
dissolutionthe residue was dissolved in acetic acid (0.75 mL)
stirringthe mixture was stirred at 100° C. for 1 hour
concentrationThe mixture was concentrated
additionthe residue was treated with water
customThe precipitate was collected
washwashed with water
customdried in a vacuum oven

Sources & evidence

ORD record: ord-83cfb543a2dd4f369be8c3fec470e53a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796268B2

Reaction notes

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