Pyridine → HCID 178441863, compound

HRID 2173657Notes

Reaction equation

NC1N(CC2C=CC=CC=2)N=NC=1C(N)=O.N1C=CC=CC=1.C(Cl)(=O)C(C)(C)C.[CH2:30]([N:37]1[C:41]([NH:42][C:43](=O)[C:44]([CH3:47])([CH3:46])[CH3:45])=[C:40]([C:49]([NH2:51])=[O:50])[N:39]=[N:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C(=O)C.O>[CH2:30]([N:37]1[C:41]2[NH:42][C:43]([C:44]([CH3:47])([CH3:46])[CH3:45])=[N:51][C:49](=[O:50])[C:40]=2[N:39]=[N:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-amino-1-benzyl-1H-1,2,3-triazole-4-carboxamide (150 g, 691 mmol, Eq: 1.00) was suspended in N,N-dimethylacetamide (512 g, 550 ml). Pyridine (82.1 g, 83.5 ml, 1.04 mol, Eq: 1.5) was added followed by pivaloyl chloride (126 g, 129 ml, 1.04 mol, Eq: 1.5) and the reaction mixture was heated to Tj=80° C. After complete acylation (ca 1 h30), KHCO3 (347 g, 3.45 mol, Eq: 5.00) was added and the suspension was heated to Tj=155° C. to convert the 1-benzyl-5-(2,2-dimethylpropanoylamino)triazole-4-carboxamide intermediate to the product. After 18 h30 at 155° C., the reaction mixture was cooled to RT and water (3.48 kg, 3.48 l) was added dropwise within 30 Min. The light yellow suspension was stirred for 30 min at RT, 2 h at 0° C. and filtered. The filter cake was washed with cold (0-5° C.) water (600 g, 600 ml) and dried at 50° C./5 mbar to give 161.3 g of the title compound as an off-white powder. MS(m/e): 284.0 (MH+).

Workup

temperaturethe suspension was heated to Tj=155° C.
temperatureAfter 18 h30 at 155° C., the reaction mixture was cooled to RT
filtrationfiltered
washThe filter cake was washed with cold (0-5° C.) water (600 g, 600 ml)
customdried at 50° C./5 mbar

Sources & evidence

ORD record: ord-767260c3121647f09a6bd4ecbe61f921
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056866B2

Reaction notes

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