Triethylamine → HCID 86612479, compound

HRID 2080249Notes

Reaction equation

HRID 2080249 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7](C(O)=O)=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.[O:14]([C:21]1[CH:22]=C([CH:26]=[CH:27][CH:28]=1)CN)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.F[P-](F)(F)(F)(F)F.N1([O:45][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([N:58]([CH2:61][CH3:62])[CH2:59]C)C>CN(C)C=O.O>[O:14]([C:21]1[CH:22]=[C:62]([CH:26]=[CH:27][CH:28]=1)[CH2:61][NH:58][C:59]([C:2]1[N:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:45])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10948363-Phenoxy-benzylamineHCID 23130441Quinazoline-6-carboxylic acid

Product 1

HCID 86612479HCID 86612479, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of quinazoline-6-carboxylic acid obtained in Preparation Example H-3 (9 mg, 0.052 mmol) in N,N-dimethylformamide (3 mL) were added 3-phenoxybenzylamine described in Preparation Example 4 (11 mg, 0.052 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (28 mg, 0.062 mmol) and triethylamine (17 μl, 0.125 mmol), and the solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate, and concentrated. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), and the title compound (11 mg, 0.031 mmol, 50%) was obtained.

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationconcentrated
  3. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6f0238b59ea74329bbdb42625ef70b5a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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