Phenyl isocyanate → N-(5-{5-[(Anilinocarbonyl)amino]-6-chloropyridin-3-yl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 252705Notes

Reaction equation

HRID 252705 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[NH:25]([C:26]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 86620382N-(5-{5-[(Anilinocarbonyl)amino]-6-chloropyridin-3-yl}-4-methyl-1,3-thiazol-2-yl)acetamideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[5-(5-Amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (20 mg, 0.07 mmol) and phenyl isocyanate (0.023 mL, 0.21 mmol) were stirred in THF (0.6 mL) at 40° C. for 2 hours. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 8.93 minutes; 10 mg, 36%); 1H NMR Spectrum: (DMSOd6) 12.23 (1H, s); 9.56 (1H, s); 8.69 (1H, d); 8.54 (1H, s); 8.15 (1H, d); 7.48 (2H, d); 7.32 (2H, t); 7.02 (1H, t); 2.40 (3H, s); 2.16 (3H, s); Mass Spectrum: M+H+ 402 and 404.

Workup

  1. customThe reaction product was purified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-2052689389db46b7913c6aa7fe21f0af
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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