Pyridine → HCID 22993974, compound

HRID 1167826Notes

Reaction equation

HRID 1167826 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([C:20]3[S:24][C:23]([NH:25][C:26]4[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=4)=[N:22][C:21]=3[NH2:38])[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1.CN(C=O)C>C1COCC1>[NH2:38][C:21]1[N:22]=[C:23]([NH:25][C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)[S:24][C:20]=1[C:17]1[S:18][CH:19]=[C:15]([C:11]2[CH:10]=[C:9]([NH:8][C:1](=[O:3])[CH3:2])[CH:14]=[CH:13][CH:12]=2)[N:16]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 21357966HCID 21357966, compound

Product 1

HCID 22993974HCID 22993974, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (21.3 μL, 0.2250 mmol) was added to a solution of 4-(3-aminophenyl)-N2′-(3,4,5-trimethoxyphenyl)-[2,5′]bithiazolyl-2′,4′-diamine (50.0 mg, 0.1125 mmol), prepared as described in Example C(1), dissolved in pyridine (28.5 μL, 0.352 mmol), DMF (70 μL), and THF (700 μL) at −15° C. (bath temperature). After 30 minutes, the reaction was quenched with MeOH (0.5 mL), concentrated, and purified by preparative C-18 reverse-phase HPLC (gradient elution, 95% H2O/0.1% TFA/CH3CN to 5% H2O/0.1% TFA/CH3CN), giving 46 mg (82% yield) of N-{3-[4′-amino-2′-(3,4,5-trimethoxy-phenylamino)-[2,5′]bithiazolyl-4-yl]-phenyl}acetamide.

Workup

  1. customprepared
  2. customat −15° C.
  3. customthe reaction was quenched with MeOH (0.5 mL)
  4. concentrationconcentrated
  5. custompurified by preparative C-18 reverse-phase HPLC (gradient elution, 95% H2O/0.1% TFA/CH3CN to 5% H2O/0.1% TFA/CH3CN)

Sources & evidence

ORD record
ord-2ae5cc59962c4a7bbcd0ed0454f97a06
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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