Dimethylformamide dimethyl acetal → HCID 178474390, compound

HRID 1497799Notes

Reaction equation

[C:1]([NH:4][C:5]1[N:27]=[C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[C:10]([CH3:16])[C:11]([C:13]([NH2:15])=[O:14])=[CH:12][N:7]2[N:6]=1)(=[O:3])[CH3:2].CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>C1COCC1>[CH3:30][N:31]([CH3:33])/[CH:32]=[N:15]/[C:13]([C:11]1[C:10]([CH3:16])=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[C:8]2[N:7]([N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:27]=2)[CH:12]=1)=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide (Int. 22, 100 mg, 0.27 mmol) in THF (2 mL) was added N,N-dimethylformamide dimethyl acetal, (53 μL, 0.40 mmol) and the reaction mixture was heated at 100° C. for 10 mins using microwave irradiation. The solvent was removed in vacuo to afford crude 2-acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamide intermediate. To a solution of the material thus obtained in acetic acid (2 mL) was added 4-hydrazino-benzonitrile hydrochloride (43 mg, 0.25 mmol). The mixture was heated at 90° C. for 15 minutes using microwave irradiation. The solvent was removed in vacuo and the residue azeotroped with toluene (2×5 mL). The resultant residue was purified by flash chromatography eluting with a gradient of 0-100% cyclohexane in EtOAc and then with 10% MeOH in EtOAc followed by preparative C18 HPLC, eluting with a gradient of 10-90% MeCN in water (+0.1% formic acid) to afford the title compound as a white solid (15 mg).

Workup

custommicrowave irradiation
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-78315ec0002744b180b3a50a07702252
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199984B2

Reaction notes

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