Thionyl Chloride → HCID 178432346, compound

HRID 1898445Notes

Reaction equation

HRID 1898445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl: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.[C:30]([C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].[H-].[Na+]>C1COCC1.C1C=CC=CC=1>[C:30]([C:34]1[CH:35]=[CH:36][C:37]([NH:38][C:23]([C:14]2[C:15]3[O:19][C:18]([CH3:20])=[N:17][C:16]=3[C:21]3[NH:22][C:10]([NH:9][C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:11][C:12]=3[CH:13]=2)=[O:25])=[CH:39][CH:40]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 698614-Tert-ButylanilineHCID 178432356HCID 178432356, compound

Product 1

HCID 178432346HCID 178432346, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-177 using 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-55, 0.100 g, 0.276 mmol), benzene (4 mL), thionyl chloride (5.0 mL), 4-tert-butylaniline (0.123 g, 0.828 mmol), THF (5.0 mL) and 60% NaH (0.033 g, 0.825 mmol). The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.28 (s, 9H), 2.65 (s, 3H), 6.54 (s, 1H), 7.37 (d, J=7.8 Hz, 3H), 7.60-7.68 (m, 4H), 9.43 (s, 1H), 9.93 (s, 1H), 11.56 (s, 1H); MS [M+H]+: 508.57.

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-c377308c296e4e5bb9ef8c886b3b0079
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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