Sodium Iodide → HCID 58346425, compound

HRID 222033Notes

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]([O:27][CH2:28][C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=6)=[C:23]([Cl:35])[CH:22]=5)[N:17]=[CH:18][N:19]=[C:14]4[S:13][C:10]=32)=[N:5]1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:35][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:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)[CH:12]=5)[CH:26]=[CH:25][C:24]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring solution of 2-(2-bromoethyl)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (100 mg, 0.16 mmol) in DMF (4 mL) were sequentially added 1-methyl-piperazine (0.023 mL, 0.24 mmol), sodium iodide (23.8 mg, 0.16 mmol), and sodium carbonate (33.6 mg, 0.32 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 removed under reduced pressure. The crude product was purified via reverse phase HPLC to afford the desired product (32 mg, 34%) as a white solid. 1H-NMR (DMSO-d6) δ 8.58 (d, 1H), 8.40 (s, 1H), 8.36 (s, 1H), 7.93 (s, 1H), 7.83 (dd, 1H), 7.78 (s, 1H), 7.47-7.59 (m, 2H), 7.31 (dd, 1H), 7.19 (d, 1H), 5.25 (s, 2H), 4.12 (t, 2H), 3.35 (t, 2H), 2.85 (t, 2H), 2.63 (t, 2H), 2.35-2.45 (br s, 4H), 2.22-2.32 (br s, 4H), 2.12 (s, 3H); LCMS RT=2.18 min; [M+H]+=587.4.

Workup

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

Sources & evidence

ORD record: ord-89be956b9e9643cd8fd98dbd0a13ed2e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207172B2

Reaction notes

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