Sodium Iodide → HCID 86593416, compound

HRID 1247839Notes

Reaction equation

HRID 1247839 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([NH:29][CH:30]=[O:31])[CH:6]=[N:5]1.[H-].[Na+].Br[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].[I-].[Na+].S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[CH:30]([N:29]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:7]1[CH:6]=[N:5][N:4]([CH2:3][CH2:2][OH:1])[C:8]=1[NH:9][C:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 86593417HCID 86593417, compound

Product 1

HCID 86593416HCID 86593416, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]formamide (2 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (213 mg, 60% oil suspension) under a nitrogen stream at, 0° C., and the whole mixture was stirred at 0° C. for 20 minutes. A solution of tert-butyl (3-bromopropyl)carbamate (1.27 g) in N,N-dimethylformamide (10 ml) and sodium iodide (799 mg) were added to the above solution, and the mixture was stirred overnight. 10% Aqueous potassium hydrogen sulfate solution (5 ml) was added, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave an oil, which was chromatographed on silica gel eluting with dichloromethane-ethyl acetate (2:1) to give tert-butyl (3-{N-formyl-N-[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}propyl)carbamate (1 g). The NMR spectrum of this compound indicates the existence of its rotamer.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure
  6. customgave an oil, which
  7. customwas chromatographed on silica gel eluting with dichloromethane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6daf85eed7b944178966a26b3877eca6
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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