4-Methylmorpholine → 4-[3-(3-Trifluoromethoxy-benzoylamino)-benzylamino]-quinazoline-8-carboxylic acid amide

HRID 578708Notes

Reaction equation

HRID 578708 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7](C(O)=O)=[CH:6][CH:5]=1.CCN=C=NCCC[N:23]([CH3:25])C.C1C=CC2N([OH:35])N=NC=2C=1.CN1CCOCC1.N[C:44]1[CH:64]=[CH:63][CH:62]=[CH:61][C:45]=1[CH2:46][NH:47][C:48]1[C:57]2[C:52](=[C:53]([C:58]([NH2:60])=[O:59])[CH:54]=[CH:55][CH:56]=2)[N:51]=[CH:50][N:49]=1>CN(C=O)C>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:11][CH:12]=1)[C:25]([NH:23][C:64]1[CH:44]=[C:45]([CH:61]=[CH:62][CH:63]=1)[CH2:46][NH:47][C:48]1[C:57]2[C:52](=[C:53]([C:58]([NH2:60])=[O:59])[CH:54]=[CH:55][CH:56]=2)[N:51]=[CH:50][N:49]=1)=[O:35]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 676134-(Trifluoromethoxy)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 667639594-(2-Amino-benzylamino)-quinazoline-8-carboxylic acid amide

Product 1

HCID 667635504-[3-(3-Trifluoromethoxy-benzoylamino)-benzylamino]-quinazoline-8-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.3 mg (0.1 mmol) 4-trifluoromethoxy-benzoic acid were dissolved in 1 ml DMF. 41.8 mg (0.2 mmol) EDCI, 15.0 mg (0.1 mmol) HOBt and 48.5 μl (0.4 mmol) 4-methylmorpholine were added and the mixture was stirred for 15 min. Subsequently, 50 mg (0.1 mmol) 4-(2-Amino-benzylamino)-quinazoline-8-carboxylic acid amide were added and the mixture was stirred overnight at room temperature. The reaction mixture was purified using preoperative HPLC and converted into the hydrochloride salt by treatment with excess HCl in methanol. 18.3 mg, off-white solid.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-d022cf6a800d414195634fc451bbf7c2
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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