3-Chloroaniline → HCID 66635560, compound

HRID 2204766Notes

Reaction equation

HRID 2204766 reaction equation
[Cl:1][C:2]1[C:3]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:60][C:61]1[CH:62]=[C:63]([CH:65]=[CH:66][CH:67]=1)[NH2:64]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:19]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:20])=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:64][C:63]1[CH:65]=[CH:66][CH:67]=[C:61]([Cl:60])[CH:62]=1)=[O:9]

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66611788HCID 66611788, compound

Product 1

HCID 66635560HCID 66635560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 67; 90 mg, 0.24 mmol) in N,N-dimethylformamide (3 ml) was added diisopropylethylamine (0.08 ml, 0.48 mmol), HATU (164 mg, 0.43 mmol) and 3-chloroaniline (0.03 ml, 0.29 mmol). The solution was stirred for 2 hours and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, (solute, 1:1 ethyl acetate/cyclohexane) to yield the title compound as a white solid. 55 mg.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was purified by column chromatography (SiO2, (solute, 1:1 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-580f13fb3cc0401e81789962967b2a33
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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