N,N-Dimethyl-1,3-propanediamine → tert-Butyl 4-(2-(3-(Dimethylamino)propylamino)quinazolin-4-ylamino)piperidine-1-carboxylate

HRID 215920Notes

Reaction equation

HRID 215920 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:26][N:27]([CH2:29][CH2:30][CH2:31][NH2:32])[CH3:28]>O1CCOCC1>[CH3:26][N:27]([CH3:28])[CH2:29][CH2:30][CH2:31][NH:32][C:2]1[N:11]=[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 58006142tert-Butyl 4-((2-chloroquinazolin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 58006221tert-Butyl 4-(2-(3-(Dimethylamino)propylamino)quinazolin-4-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(2-chloroquinazolin-4-ylamino)piperidine-1-carboxylate (3.34 g. 9.21 mmol) and 3-(N,N-dimethyl amino)propylamine (2.9 ml, 23.03 mmol) in dioxane (15 ml) in a sealed-tube were heated to 120° C. overnight. The solvent was removed and the crude product was purified by silica gel column chromatography using 10% NH3 ca. 7 N MeOH in CH2Cl2 and 90% CH2Cl2 solution as eluent to produce the title compound as a pure white solid.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ae9a2c78d9545a0ae06543e43d2e61b
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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