Diisopropyl diazene-1,2-dicarboxylate → tert-Butyl 3-(2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenoxy)propylcarbamate

HRID 1878312Notes

Reaction equation

HRID 1878312 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].[Br:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]2[CH:39]=[C:38]([C:40]3[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=3O)[NH:37][N:36]=2)=[N:32][CH:33]=1>C1COCC1>[Br:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]2[CH:39]=[C:38]([C:40]3[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=3[O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[NH:37][N:36]=2)=[N:32][CH:33]=1

Participants

5

Reactant 3

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 1363378112-(3-(5-Bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenol

Product 1

HCID 86654391tert-Butyl 3-(2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenoxy)propylcarbamateYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (1.73 mL, 8.76 mmol) is added to a stirred solution of tert-butyl 3-hydroxypropylcarbamate (0.83 mL, 4.83 mmol), 2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenol) (1.59 g, 4.38 mmol) and polystyrene triphenylphosphine (5.91 g, 8.76 mmol) in THF (50 mL) at room temperature. After stirring for 45 min, the reaction is filtered, and the solvent is removed under reduced pressure. The resulting residue is chromatographed (methanol/CH2Cl2) to afford 1.27 g (54%) of a yellow solid.

Workup

  1. filtrationthe reaction is filtered
  2. customthe solvent is removed under reduced pressure
  3. customThe resulting residue is chromatographed (methanol/CH2Cl2)

Sources & evidence

ORD record
ord-5f05a11c5db145a0b3799dda02358add
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

Loading…