Sodium Iodide → HCID 58691336, compound

HRID 1594472Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=[CH:21][CH:20]=2)[CH:13]=1.Cl.Cl[CH2:34][CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH3:41].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>O.CC(C)=O>[CH3:41][N:37]1[CH2:38][CH2:39][CH2:40][CH:36]1[CH2:35][CH2:34][O:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=[CH:21][CH:20]=2)[CH:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(4-(6-(2-hydroxy-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)-acetamide (89 mg, 0.2 mmol, prepared as described in WO04014871), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (56 mg, 0.3 mmol, Aldrich), sodium carbonate (62 mg, 0.6 mmol, Aldrich), sodium iodide (45 mg, 0.3 mmol) and acetone (1 mL) was heated in a microwave synthesizer at 150° C. for 40 min. The reaction mixture diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (10% MeOH/CH2Cl2) to give the title compound as an amorphous solid. MS (ESI, pos. ion.) m/z: 558 (M+1).

Workup

extractionextracted with EtOAc (2×20 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-73fb5bf3c6c2471f91040e437fee93e5
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07301022B2

Reaction notes

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