tert-Butanol → HCID 44466334, compound

HRID 415494Notes

Reaction equation

HRID 415494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:17](=[O:18])[N:9]2[CH:10]=[C:11](C(O)=O)[CH:12]=[CH:13][C:8]2=[N:7]1.C([N:25]([CH2:28]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:17](=[O:18])[N:9]2[CH:10]=[C:11]([NH:25][C:28](=[O:37])[O:51][C:47]([CH3:50])([CH3:49])[CH3:48])[CH:12]=[CH:13][C:8]2=[N:7]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44466336HCID 44466336, compound

Product 1

HCID 44466334HCID 44466334, compound

Conditions

Temperature
160 °C

Procedure

In a 2 mL Smith Process™ vial 2-(3,4-dichlorobenzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (0.142 mmol) was dissolved in t-butanol (2 mL) and triethylamine (0.17 mmol) was added, followed by DPPA (0.17 mmol). The reaction mixture was heated at 160° C. for 30 minutes in Emrys Optimizer™ microwave reactor. The reaction mixture was concentrated and partitioned between water and chloroform. Organic layer was dried over MgSO4, concentrated, and chromatographed on silica gel using 5% MeOH in CH2Cl2 as eluent. The product tert-butyl 2-(3,4-dichlorobenzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-6-ylcarbamate was isolated as pink oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between water and chloroform
  3. dry with materialOrganic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 5% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-b9885789030846709f51987bdd1d8aa2
Source dataset
uspto-grants-2012_01
Patent number
US08088792B2

Reaction notes

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