Sodium Iodide → HCID 58346500, compound

HRID 222014Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3[C:15]4=[C:16]([NH:20][C:21]5[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=5)[N:17]=[CH:18][N:19]=[C:14]4[S:13][C:10]=32)=[N:5]1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:28][C:23]1[CH:22]=[C:21]([NH:20][C:16]2[N:17]=[CH:18][N:19]=[C:14]3[S:13][C:10]4[C:11]5[C:6]([CH2:7][CH2:8][C:9]=4[C:15]=23)=[N:5][N:4]([CH2:3][CH2:2][N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)[CH:12]=5)[CH:26]=[CH:25][C:24]=1[F:27]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring solution of 2-(2-bromoethyl)-N-(3-chloro-4-fluorophenyl)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (100 mg, 0.2 mmol) in DMF solution (5 mL) were sequentially added 1-methyl-piperazine (0.03 mL, 0.31 mmol), sodium iodide (31.3 mg, 0.21 mmol), and sodium carbonate (44.3 mg, 0.42 mmol). The mixture was stirred at 60° C. for 4 h, after which time the contents were allowed to cool to rt and the solvent then removed under reduced pressure. The crude product was purified via reverse phase HPLC to afford the desired product (66 mg, 63%) as a white solid. 1H-NMR (CD3OD) δ 2.25 (s, 3H), 2.40-2.60 (m, 8H), 2.76 (t, 2H), 2.95 (t, 2H), 3.28 (t, 2H), 4.17 (t, 2H), 7.10 (t, 1H), 7.45-7.50 (m, 1H), 7.69 (s, 1H), 7.84 (dd, 1H), 8.42 (s, 1H); LCMS RT=2.46 min; [M+H]+=498.2.

Workup

temperatureto cool to rt
customthe solvent then removed under reduced pressure
customThe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record: ord-0c1ded801ddd4f53ade17e47c37d1301
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207172B2

Reaction notes

Loading…