Hydrochloric Acid → HCID 56942472, compound

HRID 1507876Notes

Reaction equation

HRID 1507876 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17]4[CH:29]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[S:27][C:18]=4[N:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[C:17]4[CH:29]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[S:27][C:18]=4[N:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)[CH2:14][CH2:15]2)=[O:9])=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66758966HCID 66758966, compound

Product 1

HCID 56942472HCID 56942472, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 4-(4-(2-(4-chlorophenoxy)acetyl)piperazin-1-yl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine-2-carboxylate (0.12 g, 0.22 mmol) in methanol/2M NaOH/CH2Cl2 (5:5:1, 5 ml) was stirred at room temperature for 3 hours after which it was neutralized with a 2N HCl solution in dioxane. The solvents were removed under reduced pressure, and the crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 8:1) to yield the title compound as a pale yellow solid (50 mg, 44%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 8:1)

Sources & evidence

ORD record
ord-c329aafbdc504972a6458f0fcdecf392
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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