Benzoyl chloride → N-Benzoyl-N-[2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-yl]benzamide

HRID 32616Notes

Reaction equation

HRID 32616 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([NH2:16])[C:14]=3[N:15]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[CH:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N([CH2:37][CH3:38])CC)C.[C:39]([O-:42])(O)=O.[Na+]>N1C=CC=CC=1>[C:23]([N:16]([C:13]1[C:14]2[N:15]=[C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][C:5]=3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:8][C:9]=2[N:10]=[CH:11][N:12]=1)[C:39](=[O:42])[C:38]1[CH:37]=[CH:7][CH:6]=[CH:5][CH:17]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 103579192-(1-Methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Product 1

HCID 69194214N-Benzoyl-N-[2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-yl]benzamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(1-Methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 2) (0.56 g) was dissolved in pyridine (10 mL), benzoyl chloride (0.44 mL) and triethylamine (0.28 mL) added then stirred at ambient temperature under an inert atmosphere. After 4 hours saturated aqueous NaHCO3 (10 mL) was added, the reaction mixture filtered, washed with water, EtOAc, diethyl ether and dried under high-vacuum to give the title compound as a colourless solid (0.63 g, 68%);

Workup

  1. filtrationthe reaction mixture filtered
  2. washwashed with water, EtOAc, diethyl ether
  3. customdried under high-vacuum

Sources & evidence

ORD record
ord-93dc94d07a654fabaf3e2b2b176eb4c6
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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