2-Chloroaniline → HCID 10158684, compound

HRID 1064565Notes

Reaction equation

HRID 1064565 reaction equation
Cl.[CH3:2][C@H:3]1[N:8]([C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH3:18])[C@@H:7]([CH3:19])[CH2:6][N:5]([CH2:20][C:21]([OH:23])=O)[CH2:4]1.[Cl:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].C(N(CC)C(C)C)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Cl:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:21](=[O:23])[CH2:20][N:5]1[CH2:4][C@H:3]([CH3:2])[N:8]([C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH3:18])[C@H:7]([CH3:19])[CH2:6]1

Participants

7

Reactant 4

HCID 72402-Chloroaniline2×HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 131725227HCID 131725227, compound

Product 1

HCID 10158684HCID 10158684, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Bromo-tris-oxy-tripyrrolidinophosphonium hexafluorophosphate (known as PyBroP) (0.18 g) was added to a stirred solution of the product from step (iv) (0.14 g), 2-chloroaniline (0.05 g) and N,N-diisopropylethylamine (0.3 g) in anhydrous dimethylformamide (6 ml). After stirring for 4 hours a further aliquot of 2-chloroaniline (0.1 ml) and PyBroP (0.18 g) were added and the mixture further stirred at room temperature for four days. Water was added and the precipitate filtered to give the crude product as a brown solid (0.07 g). This was purified by high pressure liquid chromatography (acetonitrile/0.1% aqueous ammonium acetate, gradient elution 25% to 75% organic phase) to give the title product as a white solid. Yield 0.04 g.

Workup

  1. additionwere added
  2. filtrationthe precipitate filtered
  3. customto give the crude product as a brown solid (0.07 g)
  4. customThis was purified by high pressure liquid chromatography (acetonitrile/0.1% aqueous ammonium acetate, gradient elution 25% to 75% organic phase)

Sources & evidence

ORD record
ord-6f9dcbc113b443dfa921df4ab858ebb6
Source dataset
uspto-grants-2005_11
Patent number
US06969713B2

Reaction notes

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