Diisopropylethylamine → {2-[4-(2-Dimethylaminoethoxy)-phenyl]-5-fluoro-3-phenyl-furo[2,3-b]pyridin-4-yl}-[1,3]-dithiolan-2-ylmethylamine

HRID 2243595Notes

Reaction equation

HRID 2243595 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[O:9][C:10]([C:18]3[CH:29]=[CH:28][C:21]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=12.[S:30]1[CH2:34][CH2:33][S:32][CH:31]1[CH2:35][NH2:36].C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][O:22][C:21]1[CH:28]=[CH:29][C:18]([C:10]2[O:9][C:4]3=[N:5][CH:6]=[C:7]([F:8])[C:2]([NH:36][CH2:35][CH:31]4[S:32][CH2:33][CH2:34][S:30]4)=[C:3]3[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12372267(1,3-Dithiolan-2-yl)methanamineHCID 58608099(2-[4-(4-Chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]ethyl)dimehtylamine

Product 1

HCID 58608111{2-[4-(2-Dimethylaminoethoxy)-phenyl]-5-fluoro-3-phenyl-furo[2,3-b]pyridin-4-yl}-[1,3]-dithiolan-2-ylmethylamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

The mixture of (2-[4-(4-chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]-ethyl)-dimehtylamine (7) (30.0 mg, 0.07 mmol), 1,3-dithiolan-2-methylamine (65.8 mg, 0.49 mmol) and diisopropylethylamine (63.0 mg, 0.49 mmol) in NMP (0.6 mL) was heated to 150° C. with stirring under N2 overnight. The reaction mixture was purified by silica gel column chromatography, eluting with DCM/MeOH, 9/1, to give the title compound. MS (m/z), M+H+ 510.0.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography
  2. washeluting with DCM/MeOH, 9/1

Sources & evidence

ORD record
ord-09a032eed2a346ecb3e45818e25e4bc2
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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