Pyrrolidine → 2-(pyrrolidin-1-ylmethyl)-N-(4-(trifluoromethyl)phenyl)-7-(3-(trifluoromethyl)pyridin-2-yl)quinazolin-4-amine

HRID 1791237Notes

Reaction equation

HRID 1791237 reaction equation
Cl.Cl[CH2:3][C:4]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[C:11]2[C:6](=[CH:7][C:8]([C:25]3[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:9][CH:10]=2)[N:5]=1.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[N:35]1([CH2:3][C:4]2[N:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:11]3[C:6](=[CH:7][C:8]([C:25]4[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][N:26]=4)=[CH:9][CH:10]=3)[N:5]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22030171[2-Chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine hydrochloride

Product 1

HCID 220302732-(pyrrolidin-1-ylmethyl)-N-(4-(trifluoromethyl)phenyl)-7-(3-(trifluoromethyl)pyridin-2-yl)quinazolin-4-amine

Procedure

Heat a solution of [2-chloromethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine HCl (30 mg, 0.058 mmol) in pyrrolidine (1 mL) at 100° C. for 1 hour. Remove the excess pyrrolidine under reduced pressure and partition the residue between EtOAc and 10% NaOH solution. Dry the EtOAc layer (Na2SO4) and concentrate under reduced pressure to give [2-Pyrrolidin-1-ylmethyl-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-yl]-(4-trifluoromethyl-phenyl)-amine as a foam. Mass Spec 517.2.

Workup

  1. customRemove the excess pyrrolidine under reduced pressure
  2. custompartition the residue between EtOAc and 10% NaOH solution
  3. dry with materialDry the EtOAc layer (Na2SO4)
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-87c2238b1c034b13987037b2f6511d44
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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