Hydrazine → HCID 46868853, compound

HRID 2097997Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:22]([NH2:24])=O)=[C:5]([NH:8][C:9](=[O:21])[CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)[S:6][CH:7]=1)#[N:2].C[N:26]([CH:28](OC)OC)C.[NH2:33]N>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:22]2[NH:24][N:26]=[CH:28][N:33]=2)=[C:5]([NH:8][C:9](=[O:21])[CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)[S:6][CH:7]=1)#[N:2]

Participants

Conditions

Temperature: 95 °C

Procedure

The title compound was prepared from 4-cyano-2-(2-(isoquinolin-5-yl)acetamido)thiophene-3-carboxamide (15 mg) according to protocol C except that DCM was added to the DMF-DMA step and refluxed while the hydrazine step was heated at 90° C. (rather than 95° C.). The product was purified via prep. HPLC to give N-(4-cyano-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(isoquinolin-5-yl)acetamide. Method[7], MS (ESI) 361.1 [M+H], rt=1.273 min; 1H-NMR (300 MHz, CD3OD) δ 9.62 (b s, 1H), 8.60-8.57 (m, 1H), 8.44-8.37 (m, 2H), 8.34 (s, 1H), 8.29-8.20 (m, 1H), 8.04-8.0 (m, 1H), 7.86 (s, 1H), 4.56 (s, 2H).

Workup

customThe product was purified via prep

Sources & evidence

ORD record: ord-330a9af3e4cf41baafb3ae959898b1f6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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