Ammonium Chloride → HCID 11404298, compound

HRID 2102800Notes

Reaction equation

HRID 2102800 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.Cl[C:17]([O:19][CH2:20][CH2:21][CH:22]=[CH2:23])=[O:18].[Cl-].[NH4+]>N1C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[NH:14][C:11]1[N:10]=[CH:9][C:8]2[CH2:7][CH2:6][C:5]3[N:15]=[C:2]([CH3:1])[S:3][C:4]=3[C:13]=2[N:12]=1)[CH2:21][CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33865263-Butenyl chloroformateHCID 112874152-methyl-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-amine

Product 1

HCID 11404298HCID 11404298, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (100 mg, 0.46 mmol) in pyridine (3 mL) was added 3-butenyl chloroformate (68 μL, 74 mg, 0.55 mmol). The mixture was stirred at room temperature for 16 h. Ammonium chloride solution was added (50 mL) and the product was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum to give a yellow solid. Crystallisation from EtOAc afforded the pure title product as yellow crystals (122 mg, 84%): mp 204° C. (dec). Anal. RP-HPLC: tR 14.1 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.36 (s, 1H, Py-H), 7.49 (brs, 1H, NH), 5.90-5.75 (m, 1H, CH), 5.19-5.07 (m, 2H, CH2), 4.27 (t, 2H, J 6.6, CH2), 3.06 (m, 4H, CH2—CH2), 2.77 (s, 3H, CH3), 2.45 (m, 2H, CH2). MS (ESI+): m/z 339.00 (M+Na)+.

Workup

  1. extractionthe product was extracted with CH2Cl2 (3×50 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a yellow solid
  6. customCrystallisation from EtOAc

Sources & evidence

ORD record
ord-4d0f4395f519407abdd7df14762ab78a
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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