Sodium Thiosulfate → HCID 86711289, compound

HRID 336154Notes

Reaction equation

HRID 336154 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]2[C:18]([C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][N:16]([CH2:29][CH2:30][C@@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:32]=[CH2:33])[C:12]=2[N:13]=[CH:14][N:15]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1>[NH2:9][C:10]1[C:11]2[C:18]([C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:17]([Br:1])[N:16]([CH2:29][CH2:30][C@@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:32]=[CH2:33])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 86711288HCID 86711288, compound

Product 1

HCID 86711289HCID 86711289, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-bromosuccinimide (1.35 g) in THF (23 ml) was added to a solution of (R)-tert-butyl (5-(4-amino-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pent-1-en-3-yl)carbamate (3.21 g) obtained in Step 6 in THF (26 ml) under ice-cooling over 30 minutes. The mixture was stirred under ice-cooling for 30 minutes. After adding a 5% aqueous sodium thiosulfate solution, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol) to obtain the title compound as a light-brown solid (3.15 g).

Workup

  1. temperaturecooling over 30 minutes
  2. temperaturecooling for 30 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-73735d0203364a65a66c40b313e56aab
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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