Sodium Iodide → 1-[({5-[6-Bromo-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3,4-oxadiazol-2-yl}methyl)amino]-3-(4-morpholinyl)-2-propanol

HRID 38847

Reaction equation

HRID 38847 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([CH2:25]Cl)=[N:23][N:24]=2)[CH:3]=1.[I-].[Na+].[NH2:29][CH2:30][CH:31]([OH:39])[CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([CH2:25][NH:29][CH2:30][CH:31]([OH:39])[CH2:32][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[N:23][N:24]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 28322311-Amino-3-(morpholin-4-yl)propan-2-olHCID 666956686-bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole

Product 1

HCID 666939741-[({5-[6-Bromo-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3,4-oxadiazol-2-yl}methyl)amino]-3-(4-morpholinyl)-2-propanolYield 57.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

6-Bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole (300 mg, 0.661 mmol) and sodium iodide (138 mg, 0.921 mmol) were weighed into a round-bottomed flask and dissolved in acetonitrile (2 ml) before 1-amino-3-morpholin-4-ylpropan-2-ol (212 mg, 1.322 mmol, available from Enamine Ltd) and DIPEA (0.231 ml, 1.322 mmol) were added. The mixture was heated to 70° C. for 2 h, then cooled, diluted with DCM and washed with 2 M aqueous HCl (5 ml). The organic layer was separated with a hydrophobic frit and the aqueous layer was neutralised to pH 7 by addition of 2M NaOH resulting in the formation of a solid precipitate. This was filtered off under vacuum and dried in air for 2 h to give the title compound as a cream solid (220 mg).

Workup

  1. additionwere added
  2. temperaturecooled
  3. washwashed with 2 M aqueous HCl (5 ml)
  4. customThe organic layer was separated with a hydrophobic frit
  5. additionthe aqueous layer was neutralised to pH 7 by addition of 2M NaOH resulting in the formation of a solid precipitate
  6. filtrationThis was filtered off under vacuum
  7. customdried in air for 2 h

Sources & evidence

ORD record
ord-95cfe6ba095344a59fe51b25ad0543af
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Linked notes

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