Diethyl Ether → HCID 178433125, compound

HRID 1715295Notes

Reaction equation

C([N:4]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][C:12]([C:16](=O)[CH2:17]Br)=[C:13]([CH3:15])[N:14]=2)=[N:5]1)(=O)C.Br.C(N1C=CC(NC2SC(C(=O)CBr)=C(C)N=2)=N1)(=O)C.[C:40]([CH2:42][C:43]([NH2:45])=[S:44])#[N:41].CCOCC>CCO>[CH3:15][C:13]1[N:14]=[C:10]([NH:9][C:6]2[CH:7]=[CH:8][NH:4][N:5]=2)[S:11][C:12]=1[C:16]1[N:45]=[C:43]([CH2:42][C:40]#[N:41])[S:44][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-{2-[(1-acetyl-1H-pyrazol-3-yl)amino]-4-methyl-1,3-thiazol-5-yl}-2-bromoethanone, (Intermediate 4) (150 mg; 0.35 mmol; 1 eq.) in EtOH (5 ml) is added 2-cyanothioacetamide (35.4 mg; 0.35 mmol; 1 eq.). The resulting mixture is heated 10 min at 60° C., 10 min at 70° C. and 10 min at 80° C. under microwave action. As the reaction is complete, Et2O is added. The resulting precipitate is filtered and washed with Et2O, affording Compound (55) as beige solid (84.1 mg; 62%). 1H NMR (DMSO-d6) δ 2.46 (s, 3H), 4.61 (s, 2H), 6.01 (d, J=2 Hz, 1H), 7.65 (s, 1H), 7.72 (d, J=2 Hz, 1H), 11.26 (br s, 1H). M− (ESI): 301.13; M+ (ESI): 303.14. HPLC (method A), Rt: 1.84 min (purity: 92.7%).

Workup

filtrationThe resulting precipitate is filtered
washwashed with Et2O

Sources & evidence

ORD record: ord-84148c066a0f4e1c99e7e160bbc77a87
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799814B2

Reaction notes

Loading…