P-Anisidine → HCID 59813198, compound

HRID 1925331Notes

Reaction equation

HRID 1925331 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20](O)=[O:21])=[CH:15][CH:14]=[CH:13]3)[CH:6]=[CH:5][N:4]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[O:21])=[CH:15][CH:14]=[CH:13]3)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 24823895HCID 24823895, compound

Product 1

HCID 59813198HCID 59813198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(2-Methylaminopyridin-4-yloxy)-1-naphthoic acid (170 mg, 0.58 mmol), p-anisidine (107 mg, 0.87 mmol), DIPEA (149 mg, 1.16 mmol) and TBTU (223 mg, 0.69 mmol) were combined in DMF (3.0 mL) and the reaction mixture was stirred at RT for 16 h, quenched by addition of a 6M aqueous NaOH solution. The precipitate was filtered off, treated with DCM, sonicated. The title compound was isolated by filtration. MS (ESI, pos. ion) m/z: 400.1 (M+1). Mass Calc'd for C24H21N3O3: 399.45.

Workup

  1. customquenched by addition of a 6M aqueous NaOH solution
  2. filtrationThe precipitate was filtered off
  3. additiontreated with DCM
  4. customsonicated

Sources & evidence

ORD record
ord-680cafd8c1eb4630bb5119adb1d09d4d
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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