Benzoyl chloride → HCID 66743954, compound

HRID 2363977Notes

Reaction equation

HRID 2363977 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:15][C:14]3[C:13](=[O:16])[NH:12][C:11]4([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[NH:10][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[C:30]1([C:29]([N:19]2[CH2:20][CH2:21][C:11]3([NH:10][C:9]4[CH:8]=[C:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[S:15][C:14]=4[C:13](=[O:16])[NH:12]3)[CH2:17][CH2:18]2)=[O:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 66742948HCID 66742948, compound

Product 1

HCID 66743954HCID 66743954, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 6′-(pyridin-4-yl)-1′H-spiro [piperidine-4,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one (0.0500 g, 0.170 mmol) and triethylamine (0.070 mL, 0.51 mmol) in tetrahydrofuran (4 mL) was cooled to 0° C. in an ice bath. A solution of benzoyl chloride (0.0260 g, 0.190 mmol) in tetrahydrofuran (0.1 mL) was added, and the reaction was allowed to warm to room temperature overnight. Then, the solvent was removed and the obtained residue was diluted with methanol (25 mL) and the mixture was stirred with solid NaHCO3 (1.5 g) for 20 min. Then, the solids were removed by filtration. The filtrate was concentrated to give a yellow solid, which was triturated with water and collected by filtration. This solid product was recrystallized from hot methanol/hexanes to give the title compound (0.0315 g, 45%) as a yellow solid:

Workup

  1. customThen, the solvent was removed
  2. additionthe obtained residue was diluted with methanol (25 mL)
  3. customThen, the solids were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customto give a yellow solid, which
  6. customwas triturated with water
  7. filtrationcollected by filtration
  8. customThis solid product was recrystallized from hot methanol/hexanes

Sources & evidence

ORD record
ord-7d2417a864924d77aa7d5b44db7a6701
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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