4-Fluoroaniline → HCID 178432350, compound

HRID 1898447Notes

Reaction equation

HRID 1898447 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([OH:25])=O)=[CH:13][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[F:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:35][C:34]3[CH:36]=[CH:37][C:31]([F:30])=[CH:32][CH:33]=3)=[O:25])=[CH:13][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 97314-FluoroanilineHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 178432357HCID 178432357, compound

Product 1

HCID 178432350HCID 178432350, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-177 using 7-[(2-chloro-6-fluorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-56, 0.050 g, 0.138 mmol), thionyl chloride (2.0 mL), 4-fluoro aniline (0.052 g, 0.138 mmol), THF (5.0 mL) and 60% NaH (0.017 g, 0.692 mmol). The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH: DCM to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 2.65 (s, 3H), 7.20 (t, J=7.8 Hz, 2H), 7.40-7.46 (m, 3H), 7.63 (s, 1H), 7.80-7.82 (m, 2H), 9.34 (s, 1H), 10.08 (s, 1H), 11.63 (s, 1H); MS [M−H]−: 452.23.

Workup

  1. customThe title compound was prepared
  2. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Sources & evidence

ORD record
ord-e3d364f879bc4368b191de1a3ba6ac4c
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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