3-Fluoroaniline → HCID 69813140, compound

HRID 1029240Notes

Reaction equation

HRID 1029240 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:32]=[CH:31][C:11]2[C:12](=[O:30])[NH:13][C:14]3[C:19]([C:10]=2[CH:9]=1)=[C:18]([NH:20][C:21]1[CH:25]=[CH:24][N:23]([CH2:26][C:27](O)=[O:28])[N:22]=1)[CH:17]=[CH:16][N:15]=3)=[O:7].CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[F:58][C:59]1[CH:60]=[C:61]([CH:63]=[CH:64][CH:65]=1)[NH2:62]>C(Cl)Cl>[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:32]=[CH:31][C:11]2[C:12](=[O:30])[NH:13][C:14]3[C:19]([C:10]=2[CH:9]=1)=[C:18]([NH:20][C:21]1[CH:25]=[CH:24][N:23]([CH2:26][C:27]([NH:62][C:61]2[CH:63]=[CH:64][CH:65]=[C:59]([F:58])[CH:60]=2)=[O:28])[N:22]=1)[CH:17]=[CH:16][N:15]=3)=[O:7]

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 69810728HCID 69810728, compound

Product 1

HCID 69813140HCID 69813140, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

299 (18 mg, 0.04 mmol), DIEA (16 mg, 0.12 mmol), BOP-Cl (13 mg, 0.05 mmol), and 3-fluoroaniline (13 mg, 0.12 mmol) were suspended in CH2Cl2 (1 mL), and stirred overnight at room temperature. The crude reaction mixture was purified directly via HP-LC to provide 300 (10 mg, 37% yield) as a solid. LC-MS (M+H=543, obsd.=543).

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly via HP-LC

Sources & evidence

ORD record
ord-96de56ce4ad041c1a84f211396669ed3
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…