Dicyclohexylcarbodiimide → HCID 14792152, compound

HRID 979482Notes

Reaction equation

HRID 979482 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[C:22]([NH:29][C@H:30]([C:34](O)=[O:35])[CH:31]([CH3:33])[CH3:32])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:22]([NH:29][C@H:30]([C:34]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)[CH2:6][CH2:7]1)=[O:35])[CH:31]([CH3:32])[CH3:33])([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 14792148HCID 14792148, compound

Product 1

HCID 14792152HCID 14792152, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Amino-1-(6,7-dimethoxyquinazolin-4-yl)piperidine (0.9 g) was added to a mixture of Boc-L-valine (1.3 g), N,N'-dicyclohexylcarbodiimide (0.7 g) and acetonitrile (30 ml) while cooling with ice. The mixture was further stirred at room temperature for 30 minutes. Insoluble substances were removed from the reaction solution by filtration. The filtrate was concentrated and partitioned between ethyl acetate and a saturated aqueous solution of NaHCO3. The organic layer was dried over anhydrous magnesium sulfate and concentrated. By purification using a 40 g silica gel column, 4(Boc-L-valyl)amino-1-(6,7-dimethoxyquinazolin-4-yl)piperidine (1 g, 74%) was obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customInsoluble substances were removed from the reaction solution by filtration
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customBy purification

Sources & evidence

ORD record
ord-06f37d76e6de426ab8a4080d66532961
Source dataset
uspto-grants-1987_05
Patent number
US04668683

Reaction notes

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