Acetyl chloride → HCID 58094900, compound

HRID 2282332Notes

Reaction equation

HRID 2282332 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH2:23])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])[CH:2]=[CH2:3].[C:32](Cl)(=[O:34])[CH3:33]>N1C=CC=CC=1>[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH:23][C:32](=[O:34])[CH3:33])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 58095014HCID 58095014, compound

Product 1

HCID 58094900HCID 58094900, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl][1,3]thiazolo[5,4-d]pyrimidin-2-amine (200 mg, 0.41 mmol) and pyridine (20 mL), was added acetyl chloride (0.30 mL, 4.2 mmol) at rt. After being stirred for 1 hour, acetyl chloride (0.30 mL, 4.2 mmol) was added at rt. After being stirred for 2 hours, the mixture was concentrated in vacuo. To the residue, were added sat. NaHCO3 and EtOAc. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ether to yield the title compound (204 mg, 90%) as a pale yellow solid. LCMS: (AA) ES+527, 529. 1H NMR (400 MHz, d6-DMSO) δ: 12.76 (s, 1H), 8.97 (s, 1H), 8.68 (s, 1H), 7.77 (d, J=2.3 Hz, 1H), 7.44 (dd, J=8.3, 2.3 Hz, 1H), 7.26-7.23 (m, 2H), 7.04 (d, J=1.3 Hz, 1H), 5.70-5.62 (m, 1H), 5.09-5.06 (m, 1H), 4.85-4.80 (m, 1H), 4.38 (d, J=5.3 Hz, 2H), 2.25 (s, 3H).

Workup

  1. stirringAfter being stirred for 2 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. additionTo the residue, were added sat. NaHCO3 and EtOAc
  4. stirringAfter being stirred for 30 min
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with ether

Sources & evidence

ORD record
ord-a380bd73926e4a1fb37e6c8294a36b22
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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