3-(4H-1,2,4-Triazol-4-yl)propan-1-ol → 4-[7-(3-[1,2,4]Triazol-4-yl-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 657258Notes

Reaction equation

HRID 657258 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20](F)=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:25]1[N:26]=[CH:27][N:28]([CH2:30][CH2:31][CH2:32][OH:33])[CH:29]=1.CC([O-])(C)C.[K+]>COCCOC.CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:33][CH2:32][CH2:31][CH2:30][N:28]4[CH:27]=[N:26][N:25]=[CH:29]4)=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 128883883-(4H-1,2,4-Triazol-4-yl)propan-1-olHCID 23665647Potassium tert-butoxideHCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 595517624-[7-(3-[1,2,4]Triazol-4-yl-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-(7-fluoro-quinazolin-4-yl)-piperidin-1-carboxylic acid tert-butyl ester (31.6 mg, 95.5 μmol), as prepared in Example 65b, 3-[1,2,4]-triazol-4-yl-propan-1-ol (ChemPacific) (12.0 mg, 94.5 μmol), and KOtBu (11.7 mg, 104 μmol) in DME (100 μL) and DMSO (50 μL) was stirred at rt for 1 hr. The resulting homogeneous amber solution was partitioned with DCM (2 mL) and 0.5M sodium phosphate/pH 7 (2 mL). The organic layer was concentrated to provide the crude title compound that was used immediately for the next step. LC/MS (ESI): calcd mass 438.2, found 439.1 (MH)+.

Workup

  1. customThe resulting homogeneous amber solution was partitioned with DCM (2 mL) and 0.5M sodium phosphate/pH 7 (2 mL)
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-59a9d760ceba47a5afeaea55ac4717ee
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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