1,2-Dimethoxyethane → HCID 68695049, compound

HRID 657278Notes

Reaction equation

HRID 657278 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[N:6].CC([O-])(C)C.[K+].COCCOC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[C:41]3[C:36](=[CH:37][C:38](F)=[CH:39][CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl.CC(C)=O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[C:41]3[C:36](=[CH:37][C:38]([O:1][CH2:2][CH2:3][CH2:4][C:5]#[N:6])=[CH:39][CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 2207054-hydroxybutanenitrileHCID 23665647Potassium tert-butoxideHCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68695049HCID 68695049, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

A mixture of 4-hydroxybutyronitrile (24.2 mg, 285 μmol) [Organometallics (1996), 15(4), 1236-41], KOtBu (34.8 mg, 311 μmol), and DME was stirred at rt, followed by the addition of 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (48.8 mg, 147 μmol) (prepared as described in Example 65b). The resulting homogeneous solution was stirred at rt for 2 hr, and was then directly loaded onto a 5 g Jones silica cartridge pre-equilibrated with 9:1 DCM/acetone, and eluted with 9:1→8:2 DCM/acetone to afford the title intermediate (24.5 mg, 42%) as a colorless oil. LC/MS (ESI) calcd mass 396.2, found 397.1 (MH)+.

Workup

  1. stirringThe resulting homogeneous solution was stirred at rt for 2 hr
  2. washeluted with 9:1→8:2 DCM/acetone

Sources & evidence

ORD record
ord-58b1eee3603546b78f50955a6ba68eaf
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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