Sodium Thiosulfate → HCID 71554947, compound

HRID 571397Notes

Reaction equation

HRID 571397 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([NH:13][C:14]2[N:19]=[CH:18][C:17]3[C:20]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=4)=[N:21][NH:22][C:16]=3[CH:15]=2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.C1C(=O)N([Br:37])C(=O)C1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N>[Br:37][C:15]1[C:16]2[NH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=3)[C:17]=2[CH:18]=[N:19][C:14]=1[NH:13][C:11]([NH:10][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:9])=[O:12]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 71555390HCID 71555390, compound

Product 1

HCID 71554947HCID 71554947, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-[(1R)-1-(4-chlorophenyl)ethyl]-3-[3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]urea (Example 19; 82 mg, 0.202 mmol) in MeCN (2 mL) was added NBS (47 mg, 0.262 mmol). The mixture was left to stir for 1 h at room temperature and then treated with 1N Na2S2O3, and extracted with chloroform:iPrOH (3:1, x3). The combined organics were dried (Na2SO4), concentrated in vacuo and purified by column chromatography on silica gel to yield 1-[7-bromo-3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-3-[(1R)-1-(4-chlorophenyl)ethyl]urea (42 mg, 0.086 mmol, 43%). MS ESI calc'd. for C21H19BrClN6O [M+1]+ 485, found 485.

Workup

  1. waitThe mixture was left
  2. extractionextracted with chloroform:iPrOH (3:1, x3)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-372e81abda3f4fbd9c50bbb68038b2f8
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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