Pyridine → N-(5-(3-(4-methoxyphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide

HRID 2077541Notes

Reaction equation

HRID 2077541 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[S:14][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:16][C:11]3=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.CCOCC>C(Cl)Cl>[CH3:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[N:13]=[C:12]4[S:14][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:16][C:11]4=[CH:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=2)(=[O:37])=[O:36])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 74014-Methoxybenzenesulfonyl chlorideHCID 57584994N-(5-(3-aminophenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide

Product 1

HCID 57584961N-(5-(3-(4-methoxyphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(5-(3-aminophenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide (102.6 mg, 0.361 mmol) was suspended in DCM (2.7 ml) and pyridine (0.050 ml, 0.61 mmol) and 4-methoxybenzene-1-sulfonyl chloride (107.2 mg, 0.519 mmol) were added. The reaction was stirred under nitrogen at room temperature for about 100 minutes. The, reaction was treated with Et2O and filtered. Solid washed with Et2O, MeOH, and Et2O, then collected and purified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 30 minutes) to afford N-(5-(3-(4-methoxyphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide (62.7 mg, 38% yield). MS (ESI pos. ion) m/z: 455. Calculated exact mass for C21H18N4O4S2 454.

Workup

  1. customThe, reaction
  2. filtrationfiltered
  3. washSolid washed with Et2O, MeOH, and Et2O
  4. customcollected
  5. custompurified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-19a028f53aea4e898383e6b3e5ae247a
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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