Water → Benzamide, N-(4,5-dihydro-2-methylthiazolo[4,5-h]quinazolin-8-yl)-

HRID 2102798Notes

Reaction equation

HRID 2102798 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH2:14])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:15]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>N1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH:14][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 112874152-methyl-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-amine

Product 1

HCID 11151419Benzamide, N-(4,5-dihydro-2-methylthiazolo[4,5-h]quinazolin-8-yl)-Yield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (0.2 g, 0.92 mmol) in pyridine (7 mL) was added benzoyl chloride (117 μL, 142 mg, 1 mmol). The mixture was stirred at room temperature for 2 h. Water (100 mL) was added and the product was extracted into EtOAc (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum. Flash column chromatography (50% EtOAc:hexane) followed by crystallisation from EtOH afforded the title product as yellow crystals (173 mg, 59%): mp 229-231° C. Anal. RP-HPLC: tR 13.5 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.59 (s, 1H, NH), 8.44 (s, 1H, Py-H), 7.95 (m, 2H, Ph-H), 7.54 (m, 3H, Ph-H), 3.09 (m, 4H, CH2—CH2), 2.77 (s, 3H, CH3). 13C-NMR (CDCl3): δ 170.70, 165.50, 160.05, 158.04, 157.02, 155.77, 134.89, 132.66, 129.15, 128.92, 127.89, 121.44, 25.39, 24.50, 20.31. MS (ESI+): m/z 323.05 (M+H)+. Anal. (C17H14N4OS)C, H, N.

Workup

  1. extractionthe product was extracted into EtOAc (3×50 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customFlash column chromatography (50% EtOAc:hexane) followed by crystallisation from EtOH

Sources & evidence

ORD record
ord-6e68b58761a649d49f3089313bfee17b
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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