Sodium hydride → HCID 16044960, compound

HRID 1157392Notes

Reaction equation

HRID 1157392 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:11]=1)[C:7]#[N:8].[NH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:35])[CH2:33]Br)=[C:27]([Cl:36])[CH:26]=1)(=[O:24])=[O:23]>CN(C=O)C>[NH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:35])[CH2:33][O:19][C:17]2[CH:18]=[C:13]([O:12][C:10]3[CH:9]=[C:6]([C:7]#[N:8])[CH:5]=[C:4]([Cl:3])[CH:11]=3)[CH:14]=[C:15]([Cl:20])[CH:16]=2)=[C:27]([Cl:36])[CH:26]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 574436043-Chloro-5-(3-chloro-5-hydroxyphenoxy)benzonitrileHCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

Product 1

HCID 16044960HCID 16044960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid sodium hydride (18 mg, 0.458 mmol) was added in portions to a DMF solution of 128 mg (0.458 mmol) of 3-chloro-5-(3-chloro-5-hydroxyphenoxy)benzonitrile (B-4). This was stirred for 30 minutes at room temperature and then 75 mg (0.229 mmol) of solid N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (A-3) was added. The reaction was then stirred at 50° C. for 14 hours until an LC/MS analysis indicated that the reaction was complete. The product was purified by a reverse phase hplc column on a Gilson unit. Clean fractions were combined and concentrated in vacuo to give the desired product 2-1 as an amorphous solid. HRMS: measured 525.9788; theoretical 525.9793. 1H NMR (DMSO-d6): 4.91 (s, 2H), 6.80 (m, 1H), 6.89 (m, 1H), 7.03 (m, 1H), 7.48 (s, 2H), 7.54 (m, 1H), 7.60 (m, 1H), 7.77 (d, 1H), 7.85 (s, 1H), 7.91 (s, 1H), 8.02 (d, 1H), 9.87 (s, 1H).

Workup

  1. stirringThe reaction was then stirred at 50° C. for 14 hours until an LC/MS analysis
  2. customThe product was purified by a reverse phase hplc column on a Gilson unit
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ddecfb2408b4daa90ef207f9a155a2e
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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