4-Chloroaniline → HCID 58674407, compound

HRID 1994137Notes

Reaction equation

HRID 1994137 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([OH:20])=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:54][C:55]1[CH:61]=[CH:60][C:58]([NH2:59])=[CH:57][CH:56]=1>CN(C=O)C.CCOC(C)=O>[Cl:54][C:55]1[CH:61]=[CH:60][C:58]([NH:59][C:18](=[O:20])[CH2:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([O:9][C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:1]#[N:2])[CH:8]=3)=[CH:15][CH:14]=2)=[CH:57][CH:56]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58674563HCID 58674563, compound

Product 1

HCID 58674407HCID 58674407, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanoic acid (400 mg, 1.49 mmol), HATU (681 mg, 1.79 mmol), DIPEA (0.5 mL, 2.98 mmol), and 4-chloroaniline (209 mg, 1.63 mmol) in DMF (5 mL) was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with 1N HCl, 1N NaOH and brine, dried over Na2SO4 and concentrated. The resulting solid was triturated with DCM and filtered to give A-21 (187 mg, 33%). 1H NMR (300 MHz, d6-DMSO): δ 10.02 (s, 1H), 8.56 (dd, J1=0.50 Hz, J2=5.8 Hz, 1H), 7.57-7.63 (m, 3H), 7.31-7.40 (m, 4H), 7.10-7.17 (m, 3H), 2.95 (t, J=7.5 Hz, 2H), and 2.65 (t, J=7.8 Hz, 2H).

Workup

  1. washwashed with 1N HCl, 1N NaOH and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting solid was triturated with DCM
  5. filtrationfiltered
  6. customto give A-21 (187 mg, 33%)

Sources & evidence

ORD record
ord-e7c0349040cb47bb805afa9c77769017
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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